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Prologue She had come back to his little restaurant within a week which he took to be a good sign. From what the owner had told him about her, she was quite the mark; rich, single and, he had to say, gorgeous. Now all Lorne needed to do was just reel her in. In his half-baked idea of a plan, he'd try to seduce her and then, if that worked, see how much he could live off her money. He wasn't a thief, and he certainly wasn't a confidence man, but he was not above living off her if he could manage it. New York was so expensive. Plus, by his way of thinking, maybe she'd help him get the art gallery he had always wanted. It sounded like she had more than enough money to take care of him and back him. At least, that was his plan as he saw it. Little did he know that he would be the central figure in a plot of her own. One that would change his life forever. Chapter 1 "I'll have the gnocchi and a gem salad to start," she said, handing back the menu to waiter. "This is becoming your usual. I like that," Lorne responded. "Anything to drink," he said, smiling at her. He was nothing if not cute in a pretty sort of way she thought to herself. "I'm not sure what I'm in the mood for, what do you suggest?" she said coyly. "Hmm...Well, you usually have the cabernet," he said referring to the house wine they carried. "I think you should try the pinot, to change it up a bit. If you don't like it, I'll bring you the cab." She had been studying him these last several weeks when she came into the brasserie, and clearly, he had done the same. She was incredibly attractive she knew so that was to be expected. She wouldn't have much difficulty with her scheme. He was long and lanky but not too tall, perhaps 5'7". His legs were long and lean, and he had a small tight ass that she liked. His torso was scrawny as were his arms as though he had never seen the inside of the gym. The consequence, she would later find out, of an amateur running career that ended midway through his university years. His face was lean and angular, with a high cheekbone, but somehow soft; he couldn't grow a beard if his life depended on it. He wore his long, thick sandy brown hair pulled back with a thin leather hair band, a look men could only pull off in the last decade maybe. She noted that she herself owned headbands similar to the one Lorne wore. Honestly, from behind, depending on what he was wearing, you wouldn't have immediately known whether he as a man or a woman, such was the thickness of his almost shoulder length hair. Physically, he would be perfect. "I'll try a glass of the pinot, Lorne, thank you," she said with a smile and picked up her phone. "Excellent," he said as he turned and retreated to the kitchen. She watched him go over the display of her phone. She'd have to learn a little more about him, but everything looked good so far. The next step was simple enough for her, a fit and attractive woman. She would seduce him and determine if he was right for her experiment. The "experiment" as it were, was to see if she could take a person of her choosing and transform them into another person of her making. The idea wasn't like something you would see on a makeover show on TV, it was something far more diabolical than that. It would be a transformation challenge worthy of her time and maximum effort, so it had to be truly life altering to her target. Further, and to add to the challenge, Anna wasn't interested in just breaking someone down into some sort of sycophant or sex slave, nothing as prosaic as that. She wanted the transformation to be remarkable, physical and mental and of her making but fully embraced by the mark, ideally without them even knowing she was the puppet master behind it all. After perhaps a year's worth of study and scheming, she had finally settled on a scenario she felt was interesting enough, big enough and doable. She would take a heterosexual man and turn him into a heterosexual, or at least bisexual, woman. As a trained psychiatrist and psychotherapist, turned hedge fund magnate, she had both the training and the resources to give it a shot. Anna was nothing if not self-aware enough to know that she was a borderline psychopath. Technically, the proper diagnosis would have been "Machiavellianist". By her own admission she has never doubted that she had some degree of anti-social personality disorder, but she was hard to label specifically. She was certainly amoral, which played out in her work and her social life. She loved and had loved, but only under very specific conditions. In that sense, she could be fiercely loyal, as she was to her two hedge fund partners. But the rest of the world, and the relationships in it, were merely her playground and she relished in her unparalleled ability to manipulate and control those she wished to, which was most people. She had graduated Princeton and gone straight to medical school at Johns Hopkins choosing psychiatry as her specialty. But it wasn't until she did her residency at Penn that she started to pay attention to business and finance. She had had a short fling with a grad student at Wharton when she first arrived on campus. He was a douche bag, but he piqued her interest in finance, the language of business. Before long she was getting an MBA in finance, no small feat considering the rigors of the residency program. She took up practice in New York at the age of 30 and practiced in Manhattan for ten years where she flourished in more ways than one. Until arriving in New York, Anna had never really experienced situations where her own moral integrity had been tested, but dealing with the breadth and depth of depravity in the 'Big Apple' left its mark. She saw the worst of society, at least from a mental health perspective and didn't shy away from it. Oddly, she embraced it and, in that time, learned to understand the benefits of having flexible morals in today's world. It wasn't long before she had carved out a special place in the Manhattan financial elite's mental well-being. She was sought after by the Wall Street types, not only because she was stunningly beautiful but also because of her "flexibility" in prescribing various medications to the bankers and traders. That flexibility made her a lot of money, mostly under the table. Her understanding of finance only helped her channel and focus her work. Soon she was on retainer to five of the most important banks and hedge funds in the world helping focus the traders, bolstering the confidence and giving them a psychological kick in the ass when it was needed. By 35 she was worth $10 million. By 40 she was worth north of $50 million. To say she was intoxicated by the money would be an understatement. And so, three months after her 40th birthday she struck out with two partners, both from prestigious investment banks, both with similar questionable moral standards, and started her own hedge fund. She put all her money into the first fund and made almost 10 times that in three years, an unprecedented rate of return. Soon the firm was the darling of the financial world, but with that attention came the scrutiny of various legal agencies. Though they couldn't prove anything to take to a grand jury, Anna and her partners decided to curtail their most brazen tactics, insider trades, side deals, and double-dealings, so they could enjoy their wealth outside of a prison cell. The firm merely tripled their money in the following two years, and so at age 45 Anna was well ensconced in the "Tres Commas" club. The wealth served to give her the means to pursue whatever passions or projects she wanted, and it shielded her from the personal faults that would hamper the life and career of someone without her means. She freely admitted to herself she could be evil. Hell, she embraced that fact; it made her particularly good at making money. With her doctorate in psychiatry, it also made her particularly good at psycho- manipulation and perfidy. This, of course, was why Lorne wouldn't have a chance. After a short while Lorne came back with the glass of pinot, setting it down for her. He turned to leave when she called to him. "Oh, Lorne." "Yes ma'am, what can I get you?" he asked cheerfully. She was a good tipper. "It's Anna, please," she said personably. "Of course, Anna. What can I get you?" "Lorne we're going to have a drink tonight, you and me. What time shall I fetch you?" Chapter 2 Anna had first gotten the idea years before while in her practice, but it wasn't until the hedge fund made her fabulously wealthy that she really entertained the notion. Over the last several years she had kept an eye out for someone who might make a good target. Though she was fabulously wealthy, not many people knew who she was and so she could go where she liked and do what she wanted in public with no issue. She had first come across Lorne when he had started working in that little caf? on the upper east side she sometimes went to for a quiet supper and to plot her next big deal. He was the affable sort, friendly, and had those boyishly good looks which made taking him to bed that night so easy. She learned a lot about him over the next several weeks as he began to spend more and more time with her at her Manhattan apartment. Being the clinician that she still was, she took that time to analyze him down to his very being. It had not taken her long to determine that he would indeed be the perfect specimen for her experiment. Not only did he meet the physical requirements, he had the right emotional state and personal life situation needed to make her scheme work as well. To begin, he worked as an assistant during the day at some small accounting firm, and had his waiter job in the evenings to make ends meet in Manhattan. His real goal, he had told her, was to own an art gallery one day and help young artists. His mother had been an artist before she died a few years back and it had given him a new perspective. His father had never been part of the family and he was an only child so the loss of his mother, whom he had been very close to, was hard for him. Not having any close family or local friends to check on him was a huge hurdle to get over, but having the emotional traits for her to manipulate was equally as important. In particular, he had the perfect combination of emotional dependency and an addiction to earning approval. He needed to earn acceptance from those around him and from whom he deemed more powerful. He had trouble being assertive and defending him and so it wasn't difficult for her to manipulate and control him. To add to all that, he was just plain na?ve; he just couldn't understand that she could be controlling him. They spent the late fall together as she put the final touches on her plan. She figured she would start Lorne on the drugs quickly, so the estrogen had a chance to build up before it was noticeable to him. Managing the dosage and combination of drugs like estrogen and testosterone blockers could be tricky she knew, but in time, she found a solution that seemed perfect. As a part of a potential biotech investment, she had become close with a doctor in Europe who was on the cutting edge of hormone replacement therapy based on one's DNA. With some persuading, and a sizable wire transfer direct to a Panamanian account, she was able to get the required dosages of the hormone therapy mixture tailored to Lorne's body thanks to the DNA samples she had collected from his semen. It was expensive, but the effects were 3-5 times faster than traditional estrogen therapies once the second of two doses was given. Under the guise of a flu shot, she gave him a special concoction of hormones, into the only small amount of fat she could find in his ass, to allow it to slowly work into his system. With the hormones in his system, and daily "vitamins" she continued to feed him, she turned her attention toward the mental conditioning she needed to instill for success. One therapy she had grown to use reliably in her prior career was hypnosis. Strictly speaking, she couldn't make Lorne do anything he wouldn't normally do through hypnosis, it wasn't like in the movies, but it served two key purposes for her. The first was to make him comfortable enough to tell her anything. Under hypnosis she was able to explore many areas of his personality and persona. In particular, she found that he was quite liberal in his attitudes toward sexuality, gender and gender norms. She would find this was largely due to his incredibly strong connection to his deceased mother and it was clear that this would be her way into his psyche. The second important use of this technique was to put suggestions into his mind and to continue to reinforce those suggestions throughout the course of his "treatment". To that end, she spent weeks learning about Lorne's identity and then building up suggestions about femininity, and about his desire to explore his feminine side. She advocated to his unconscious that he express that desire in his mannerisms, personal hygiene and even in his personal style, clothing and hair. By late December, Anna could just start to make out the manifestations of these suggestions in him. To start, his hair was longer, now down past his shoulders, and when pushed, he said he'd skipped the hair cut to save money, which she knew was a lie. It was interesting though because his eyebrows had been groomed, as had all the stray hairs around his ears and nose. Further, whereas before he had been happy to let what little facial hair grow that he could, he had taken to shaving daily. She could tell, though, that with the strong hormones she had given him it would soon become unnecessary for the razor to touch his smooth face. Finally, and she had to admit, unexpectantly, he had pierced his ears. Well actually, he had re-pierced his left ear and pierced for the first time the right ear. He had put just small silver balls in the holes, nothing too flashy but there they were. "Darling I see you've pierced your ears," she had told him. "I love it!" she said, quick to give him positive feedback. "Do you? I wasn't sure. I figured I could take them out if I wasn't happy," he replied, sheepishly. "Don't you dare. I think their fabulous on you," she said kissing him. Positive sexual stimulus was the best and quickest way to reinforce thoughts and behaviors she knew, and she deployed it liberally. Reaching down she took his crotch in her hand. "Why don't we go to the bedroom so I can examine these studs more closely?" she said in a sultry tone. "Yes please," Lorne said with a big smile. And so, she bedded him as a form of reward for his taking action on her hypnotic suggestion, which in turn only made the suggestion take hold that much more deeply. This would be an strategy she would deploy over and over in the coming months - suggest, reward, reinforce, repeat - until she had in him what she wanted. Given how well he was responding, it was time to move into the second phase of her plan. Her idea was that after the new year, when the firm's fiscal year books were put to bed and investors were communicated to, she could isolate him at her country home out on Long Island to solidify the changes. She would use the second and final dose of the special hormones once they go there and use the relative isolation of the house to her benefit. As opposed to the city, being out there would allow her a controlled environment to oversee his changes with less variables and attention that might derail her plans. After the fiscal year end would also allow her time to focus properly. The new year came and went, and Lorne still didn't suspect anything. All was going to plan, and she was just trying to figure out how she would be able to spend enough time out in Long Island to properly tend to her quarry and still be "present" at the firm. It was mid-January when she became aware of a flu like disease being spread around China. Not only did she learn of this because the hedge fund she ran would need to be aware of any pathogens that threatened the world, but she had also been interested in epidemiology while she was in medical school and just paid attention. SARS and MERS had been near misses, in her opinion, but the implications of a flu like disease turning into a pandemic were not lost on her. It spelled opportunity. She understood immediately once infections showed up in Europe, the Middle East and here in the US what was to come. First, her firm shorted oil, transportation, hospitality and non-food retailing stock, among many others. That is, they bet against those industries and in particular bet that their stock prices would plummet. It was a massive bet and they were early in which would prove to create an outsized return. Conversely, they bought various tech stocks that allowed for communication, all because her friends in the medical world were clear that because of shortfalls in the US and other governments' reactions to the disease, containment would likely not be possible. She contemplated what the CDC would be forced to do, and the only real conclusion was that a lock down was forth coming. By the end of February, with the number of cases of this strange flu climbing in New York City, the hedge fund prepared the office to be closed and everyone headed out of town. No matter how she looked at it, she figured they'd be isolating, "social distancing" they called it, for at least three months. It was a practice that harkened back to the black plague and was one of the only effective way to stop spreading a contagion like this one. She climbed into her helicopter at the downtown Manhattan heliport and a wicked grin spread across her face. It just couldn't be any more perfect she thought as she watched the city recede. Chapter 3 Anna had provisioned her home in East Hampton with everything she could think of and made sure the home office was fully equipped to allow her to run her business remotely. Her staff thought it a little odd but found space for everything. Next, she had a few cameras installed in the bedroom, bathroom and walk in closet of the room Lorne would be using. Her partners at the firm knew and used a guy for various surveillance work, usually on executives they wanted inside information from. This was a guy who would do things without asking questions and his fees reflected that understanding. He had also done the background check on Lorne she had asked for and found that, indeed, he had no close family left and few if any close friends. Finally, she placed some clothes in Lorne's closet, a few dresses, skirts, slacks and blouses and a few sets of silk pajamas, satin nightgowns and silk bathrobes all in sizes to fit him. She took the top drawer of the built-in dresser and put various kinds of panties, as well as stockings and a few garter belts. On the low racks she placed five sets of women's shoes, all size 10, all Lorne's size. There were a couple pairs of flats, two pairs with short heels and a pair of black patent leather high heels with an ankle strap. If need be, she would explain that all the clothes as well as the cosmetics and hair accessories she put in the bathroom were hers, left for when friends visited who needed a change of clothes. When all was set, she was ready to receive her unwitting test subject. Early Saturday afternoon, the black car pulled through the security fences as they slid open and into the estate. The driver went slowly but purposefully down the driveway and pulled around the gravel cul- de-sac, preparing for its return trip to the city. Lorne got out and thanked the driver as he handed him his duffle bag. He'd not been to Anna's house in the Hampton's before and he was frankly astounded at its beauty and grandeur. The house seemed massive, at least to his city eyes; the sprawling estate allowed for solitude in a way that one wouldn't be accustomed to coming from the city. His eye followed the classic shingle clad walls up to the even more remarkable and expansive roof that topped the house. He took a deep breath noting the air was fresh and clean with a hint of the ocean that surely met the land on the other side of the main house. He walked up the front steps as the black car pulled away and hit the bell. After a short pause the door swung open and healthy-looking Asian man in khakis, a button-down shirt and a grey puffer vest opened the door. "You must be Lorne," he said cheerfully. "I'm Andrew, Dr. Kemper's house manager. Welcome!" "Oh, hello. Yes, I'm Lorne, please to meet you," he said, holding out his hand. Andrew looked at the outstretched hand. Clearly, Lorne wasn't used to being in the Hamptons. "Aren't you sweet," Andrew said with a little chuckle taking Lorne's soft hand. "Here, let me get your bag and take you back to see the doctor." Andrew took Lorne's duffle bag from him and let him pass through the doorway into a grand foyer. After closing the door, he left Lorne's bag in the foyer and led him through into a large room that extend all the way to the back of the house. To his left was a casual farm style dining table that looked nicer than anything Lorne had ever seen, and to his right was an open kitchen. It was modern but with soft country feel like the dining table. It was clear that it could not only accommodate a casual Sunday breakfast but probably large East Hampton Gala if need be. The eating area continued into a large open living room, a great room, which was oriented perpendicular to the kitchen. As Andrew entered into this space, he paused and told him this Anna's favorite room, the great room and showed him the bar to the right just where the kitchen area ended. Further down on the right past the wet bar was an open door. As they approached it Lorne looked into the spacious office, past an empty modern glass desk and through another glass wall to where Anna sat at her desk facing out to the back yard and the Atlantic ocean. Lorne was impressed with the home office space which was complete with an assistant's desk that wasn't in use. It was spacious and comfortable with wonderful built in bookshelves and all the office equipment one could need to run a small firm. Anna looked up, saw Lorne and beamed. She was truly eager to see him. She rose and quickly came around her desk and out of the office to greet him. She wrapped her arms around him warmly and kissed him. "Darling you're here. I'm so excited!" she exclaimed as she pulled her lips from his. "What can I get you? Would you like to freshen up from the car ride? Andrew, maybe show him the room he can put his things in?" she said eagerly. "I'm fine Anna, really. No need to go to any trouble." "Oh, its' no trouble, my dear," she said stroking the hair on the side of his head, wrapping it around his ear. Oh, that lovely hair she thought. "This is why Andrew is here, to get you anything you need. That and to make sure I don't go crazy. He's a life saver. Really!" "I'm fine," he said addressing Andrew. "Thank you so much." "He'll have a sparkling water, Andrew. Thank you," she said. "Of course. I'll put your things in your room while you two catch up," said Andrew and he departed back to collect Lorne's bag. "How was your trip darling? Was the car ok?" she asked turning her full attention to him. "It was great, not problems at all. I'm really happy to be here. This place is amazing!" he exclaimed looking around. "Isn't it," she said, turning him and putting her arm through his. "Come, let me show the back" She walked him back through the great room and at the end of one of the seating areas turned left toward the back of the house and to a set of large sliding glass doors. They were almost hard to make out since most of the back was glass windows, but she moved to the doors and deftly unlatched the locks, sliding one of them aside. It was a beautiful sunny day but still a bit chilly. They walked out onto a back porch; the furniture was still covered for the winter. Ahead of them, across a massive long back yard was the Atlantic. "Isn't it beautiful?" Anna asked. "I just had to have this place when I found it. Its extravagant, I know, but it's my Shangri La. And now you're here! It's perfect" she said, again turning to him kissing him. He kissed her back, thankful to be in her embrace. They broke off their kiss and walked out onto the sprawling lawn. She showed him the pool, still covered for winter, and the back of the house, somehow even more grand than the front. Anna pulled at him, leading him back to the porch saying she was getting chilly. They took the steps to the porch and continued straight back into the warm house. Andrew was there waiting with a sparkling water for Lorne, complete with lime. "oh, ah, thank you Andrew." "My pleasure. Is there anything else you need?" he asked. "Do take a sip, Lorne. Andrew is a wiz with drinks," she said, pausing to wait for him to take a mouthful. He didn't really want any water, but Andrew had gone to the trouble, so he took a sip. It was pretty good actually. He could taste just a hint of the lime. Just then the doorbell rang. Anna looked at her watch quickly. "Oh, that must be the doctor. Andrew could you go let him in and bring him back here." "Certainly ma'am," Andrew replied and headed to the front door. "Doctor?" Lorne asked. "I thought it would be a good idea for us to get booster shots. We can't be too careful with this virus floating around. I want our immune system to be at its best. I had the doctor come yesterday, not really thinking that I had missed you by a day," she lied. "So, I had his practice partner come back today to set you up. We'll have him give you the shot in the spa area so you can have some privacy." "The spa area?" Lorne asked. "Yes, it's just through there," she pointed past her office door and to a door at the end of the great room. "There's a spa room for massages, hair and makeup, that sort of thing. Then a gym and sauna. It's so much easier when they come to you. You'll love it," she said pleasantly. "It's just another reason I love this house so much." Andrew brought the doctor into the great room. "Doctor Sharma, thank you so much for fitting us in today. This is Lorne whom we spoke about," Anna said motioning to Lorne as she shook the doctor's hand. "Dr. Kemper," he said to Anna, "it's no trouble at all. This won't take but a moment Lorne," he said reassuringly. "Where would you like to do this," he asked, looking at Lorne. "I was thinking through there in the spa. For a little privacy," Anna spoke up. "That sounds fine." "Great let me show you." Anna led the two men through the great room and to a big door at the far end. She opened it and beckoned them to follow her through. The door opened into a large gym space. The end closest to them had Nautilus equipment, a Peloton bike, treadmill, weights and several balls and straps, Lorne thought for sure were used for torture. The end farthest looked more like a yoga space with soft mats and large pillows, the far wall was all mirrored. As they walked, they came to a door on their left that opened into the spa room. Lorne could see that the Sauna was just past that. "Here we are," Anna said opening the door. "Take your time, Doctor. The vials are already laid out for you as we discuss. I'll wait for you here," she said. This spa room, really two rooms, one for massage and one more of a salon, could have been in any of the world's great spas. It not only seemed to have ever imaginable piece of spa equipment including the table, a salon chair and a pedicure spa, but also all to the small apparatuses lining the counters in both rooms. Further, its d?cor was soft and soothing as well, in an oriental theme. The floor was a dark wood, but the walls were a soft cream yellow. The many built in shelves in both rooms were lined with themed decorations including a bonsai tree. The doctor walked in and put his bag down on the spa table. He opened it and pulled out a syringe. He took a step over to the counter and examine the three small vials of clear liquid, all clearly marked. "Ok, Lorne," the doctor started as he put on his gloves. "Why don't you drop your pants and I'll give you these quick as I can, get you back to your day. Now, these are only boosters, but are a pretty strong dosage so we'll get them into your fat cells so they will disperse over time. Shouldn't hurt much, but you might feel it tomorrow when you sit. Nothing too bad, I promise," he said as he inserted the syringe into the first vile, drawing out the dose. Lorne wasn't sure why Anna was always giving him vitamins and such to take. She seemed pretty protective of his health, but she was an MD so if she said it was good for him, he believed her. He unbuckled his belt, released the button from the front of his pants and pulled them down to just below his boxer shorts. He turned his back to the doctor and leaning against the spa table hooked his thumb in the waistband of the boxers, pulling them down over his buttocks as he did. The doctor cleaned the site with an alcohol swab and grabbed a pinch of his flesh before sticking the needle in. He remembered the shot he had gotten in the city several months ago and he remembered the doctor then had had a hard time getting enough of his ass check to get the shot into. This time, the doctor had no problems getting a good pinch full of flesh. "Huh. My ass is bigger," he thought to himself not taking it to mean anything other than maybe he should lay of the beer for a while. He instinctively put his hand to his belly to see if he had put some weight on. Maybe it was softer, but not really. He could still feel his abs. Just his ass got a bit bigger, maybe the tops of his thighs too if he was honest. The doctor put a small band aid on the injection site and then alternated cheeks for the next dose, again putting a small band aid on the spot the needle had entered. When done, he then asked Lorne which side he wanted the third and final dose of vitamins. Lorne opted for the right side and the doctor found a spot just below his right hip for the final, albeit smallest dose. "All set," he said as he removed the needle for the last time. "How are you feeling?" "All good, Doctor," Lorne responded. He didn't really have problems with needles, but he knew some folks passed out after getting shots. Sometimes the body just reacted that way. "Good, then we are all set. Make sure to wash your hands often, and for a good long while, like 20 seconds. Reports are this thing is bad. But hey, there are worse places to be holed up, am I right?" he grinned, giving Lorne a little tap on the shoulder as he put everything back in his bag. He took out some hand sanitizer and put a large dollop in one hand then offered some to Lorne. Both mean rubbed their hands until the sensation of wetness was replaced by a cool dryness. Soon the two were out the door and back in the gym space. Andrew had rejoined Anna and the doctor thanked her and said his goodbyes. "Yes, thank you again doctor. Andrew, why don't you walk him out and take Lorne up to his room so he can get settled," Anna said. "Darling, I have a few things to finish up in the office. Give me an hour and we'll have a cocktail, how about that?" "Yeah, of course. That will be fine." The group walked back through to the great room continuing on to the front foyer while Anna stopped at her office to connect to the camera system in Lorne's room. The "vitamins" Lorne thought he was getting were really the second course of his hormone cocktail. Well, actually he did get some vitamins in the final shot. She wasn't a monster after all. She didn't want him to get sick! This cocktail would force permanent, irreversible physical changes in the young man. It would drastically reduce his ability to make testosterone and encourage his body to start producing estrogen at levels a normal woman might. The affect would be that within roughly the next three months, Lorne would lose functionality in his gonads, that is ejaculation would be difficult if not impossible to achieve. In all likelihood even achieving an erection was likely only possible with Viagra or similar erectile drugs. Finally, his body would start to exhibit more classic feminine attributes, in particular breast tissue and fat deposits around his hips, buttocks and thighs and body hair production would subside, as it had already on his face. On the plus side, the lower testosterone would make him not only less aggressive, but probably keep him from male pattern baldness. "But who knew at this point," Anna thought. "It's all a crap shoot for now." Anna could already see the changes the last dose had produced in him over these three months, mostly in some puffiness around his chest, noticeably softer skin and plumpness in that perfect ass of his. It was all still pretty subtle but with his daily doses of estrogen she gave him and the testosterone blocker he had just been given, the results would start to show more rapidly, at least that is what the clinical trials in Europe had shown. She hoped his progression would follow suit. She clicked on her computer and brought up the spy software her man had installed. She selected an icon for his room and three boxes, one each for each of the three cameras popped up. In only a short time she saw Andrew walk into the bedroom followed by Lorne. Lorne moved to the center of the room while Andrew took his bag into the large closet and left it on a small folding luggage rack. It was a big room with a king-sized bed and a nice sitting area situated around the picture window next to the door to the balcony porch. On the other side of the room was the bathroom and walk in closet. Andrew motioned to the various aspects of the room and showed him the controls for the curtains, lights and TV then bid him adieu. Lorne closed the door behind him then turned around, with a large grin on his face. This room was huge she imagined him saying to himself. He went into the bathroom to the toilet and undid his pants. He pulled them down to his knees and inspect the three band aids before sitting down. He had taken to peeing sitting down. He wasn't really sure why, but it felt right to him, plus it was hard to miss from that close he reckoned. Cleaner that way. When he was done, he pulled his boxers and jeans back up, mindful of the bandages and buckled up the belt. He washed his hand for 20 seconds then went into the closet to unpack. It was a nice closet. The wood trim and the built-ins were not cheap. Nothing in the house was. He notices several garments still hanging on the racks which he assumed were Anna's or perhaps a friend of hers. There were a few dresses, some lovely silk and satin blouses and skirts, a few pairs of slacks and a couple of robes. He pulled out his hanging clothes, all of three shirts and a nice pair of pants and hung them next to the dresses. He grabbed a hand full of his folded clothes and went to the built-in dresser. He opened the top draw and was mildly surprised to see it full of women's underwear and lingerie. Anna watched on her screen as he lingered over the drawer, looking but not touching. He slowly closed the drawer and pulled open the next one down, stowing his clothes. He finished emptying the bag into the remaining drawers and brought his Dopp kit into the bathroom. He opened the top drawer next to the vanity to put in his few items and found it full of cosmetics, brushes and lotions. Likewise, the second drawer was full of hair styling products, a dryer and brushes. The very bottom drawer had room, so he put the whole kit in there and closed it up. He looked up at his reflection in the mirror and examined himself, turning his head slowly side to side. He couldn't see a hint of a beard and his face looked soft and smooth. His hair was a good bit longer then it had ever been, almost two inches he reckoned, but he decided he liked it. He was glad he had decided to let it grow. He pulled out one of the brushes, removed his headband and brushed out his hair so that it fell in more of a straight line down from his head and less in a full, wild sort of way he normally let it. Once done he put the hair band back in, pulling it back across his forehead and placing the ends just behind his ears to keep the hair from his face. He wasn't sure why, but it had just felt like a good idea to keep his hair looking good. Anna watched him retrace his steps into the closet. He examined himself in the full-length mirror, turning around to examine his ass. He put his hand on it, grabbing most of his right butt cheek. Anna guessed that he was noticing the relative plumpness of his derriere for the first time. He gave a sort of small shrug then looked again at the dresses. He took a step over to them and ran his hand down each of the first two dresses, examining them. "Yes, that's right dear, give them a good look," Anna said to her computer screen, thinking of some of the suggestions she had put into his head during their hypnosis sessions. Lorne went down the line looking at all of the items hanging there. He even grabbed one of the blouses and held it too him looking at himself in the mirror. "Excellent," Anna said, elated by what she saw. He put the blouse back on the bar and moved over to the dresser. He slowly opened the top drawer and gazed at the lingerie again. After a short while he reached in and pulled out one of the long satin night gowns, holding it by the straps and letting it fall to its full length in front of him. He stepped back and held it to him looking at himself again in the mirror. He spent a while examining himself and then looked over his shoulder to the closet door. He walked over and gently closed the door, locking it as he did. "Oh? And just what do you think you're doing, my dear?" Anna asked the computer. Lorne kicked off his shoes and pulled off his sweater and shirt. He then took off his jeans and boxers and donned the night gown, putting his arms through the straps and pulling it over his head to let it fall slowly down his body. When finally, it hung from his shoulders he went back to the mirror. Anna was rapt with attention He let his hands run up and down his body letting the cool fabric stroke his soft skin. He paused at his chest and seemed to caress his swollen nipples, the buds of his future breasts. He seemed to enjoy the sensation and let out a deep sighed as he let the fabric stroke his now more sensitive nipples. This was more that she had hoped for and a wicked grin worked across her face as she watched him doff the gown and put it back into the drawer, his erection evident. She would reward him tonight. She needed the progress to take. Chapter 4 Lorne came down about an hour later and Anna was talking with Andrew in the kitchen. "Hello darling!" she said when he walked in. She embraced him and gave him a quick peck on the lips. "I?m so glad you?re here," she said, still holding him looking into his eyes. She was able to inspect his hair more closely now. It looked better brushed straight and not in the masculine style he normally wore, which was to say, unkempt. She had to hold back a smile as the look of the hair pulled back with a leather headband and his soft facial skin gave him an androgynous look, if not an altogether feminine one. The conditioning was working and so she elected to do another session with him now to reinforce. "Me too," he replied. "You have a wonderful home here Anna," he added sort of looking around the massive kitchen. "Why thank you," she said stepping back. "We try, don?t we Andrew?" she asked over her shoulder. "That we do!" he replied. Anna looked back at her lover. "What did you do with your hair, darling it looks lovely," she said, reaching up and running her fingertips over his right ear. She was careful to emphasize the word "lovely" as she did. "oh, ah...I guess I brushed it out," he said, sort of sheepishly. "I love it. You need to keep doing it that way," she said. "I have some products you can use to make it look even better. Now," she said, changing the subject so he wouldn?t dwell on his hair, "Andrew is here to make us drinks, what will you have?" she asked. "Well, ah, what do you have Andrew?" he asked, not sure of what to order. "Anything and everything. Anna keeps a well-stocked bar," he said amiably. "I have to, my partners and our investors drink me out of house and home when they?re here and they have expensive taste. Andrew, I think we?ll have the 1961 Ch?teau Latour with dinner. I believe Chef Claude is making game birds. Don?t you think that would go well" she asked. "I do, so let?s start with something that won?t dull the taste buds then, yes?" he suggested. "Agreed. What do you suggest?" she asked. "I think a champagne cocktail would be perfect. Nice and light," he added. "Perfect. Ok for you Lorne?" she asked. "Yeah. Great. You know me Anna, I?m not picky about my drinks." "Excellent. Andrew bring them into the great room with some nibbles, will you?" "Certainly, I?ll meet you out there," he replied and went about getting things set. "Good," she said, turning her attention back to Lorne. "Come with me, let?s go sit," she said taking his hand and leading him back out to the great room. A couple of different seating configurations were set in the large room, but they picked the one farthest from the kitchen, closest to the door to the gym, by the massive fireplace. Andrew had already lit it in anticipation and the warmth filled the seating area nicely. The couches were all deep and soft and they fell into one while they waited for the drinks to come. They kissed again and chatted and shortly Andrew arrived with a tray of drinks and hors d'oeuvres. He set them down on the coffee table in front of them. "Thank you, Andrew. We?ll need about 45 minutes alone now, alright," she told him. "Of course. Text me when you need something." With that he turned and headed back to the kitchen to find Chef Claude who should have started his preparations by now. "Alone time?" Lorne asked with a smile. "Yes, we should do a session" she said, pulling out a small bronze ball on a chain from her pocket. "Oh," he said, recognizing the object she used to help him into his hypnotic state. "Just a short one darling then we?ll enjoy our drinks. Here, take a sip first then we?ll start." They both reached for their drinks, clinking them together and then took healthy sips, letting the bubbly liquid work down their throats. "Ok," she said, setting down her glass and sitting back. She held out the ball suspended from the chain, letting is swing freely. "Clear you mind and focus on the talisman," she said in a soothing tone using the trigger word "talisman" that helped him fall under more rapidly. Before long she had him deep in his hypnotic state. She started slowly first asking him if he was happy to be out of the city and then telling him he was happy to be there with her. Soon she moved on to the important parts. "You?ve been a good boy, Lorne," she said. "you?ve come to enjoy soft things, haven?t you? Pretty things?" "Yes" he said sort of absently, deeply in a trance. "You like soft pretty things, don?t you?" she asked. "Yes," he said. "That?s right, you do like soft pretty things," she said. She reached into her other pocket and pulled out a pair of satin panties. "Reach out your hand and take these panties. That?s it, now feel how soft and cool they feel on your face," she said. "That?s it, can you feel how soft they are. They?re very pretty," she continued. She reached over to him and started to undo his belt and pants, asking him to feel the soft cool fabric on his skin. "How does it feel Lorne? Don?t they feel nice against your skin?" she asked, reaching into his pants. "Yes," he said, exhaling hard as her hand wrapped around his member. "Yes, you like that feeling," she said starting to stroke his manhood. "You like how it feels on your skin." "Uh-huh," he whispered back. "You want to feel that soft fabric, don?t you?" she asked, pulling his rising manhood from his boxers so it was now exposed. "Yes," he said softly, intensity on his face as he felt his cock being stroked. "You want to feel the lovely, pretty fabric against your skin as often as you can, don?t you," she said continuing to stroke his almost fully erect dick. "Yes, please," he said. "Tell me you want soft, pretty things against your skin. Tell me you want to wear them," she said, pumping him more vigorously. "Yes...oh...please," he said his face screwing up as the intensity of her pumping started to drive him wild. He held the panties closed to his face, rubbing them up and down as he did. "I want to wear the pretty things against my skin," he said. "That?s right, you do. You?ve always wanted to wear the pretty things, haven?t you?" "Yes, I like pretty things." "Do you want me to let you wear the soft pretty things, Lorne?" "Yes, please," he said, a hint of begging in his soft voice. "Soft and pretty things are feminine, aren?t they? Feminine things are soft and pretty. You like the soft and pretty things like those panties, so you like feminine things, don?t you? Soft and pretty things are feminine. Do you want me to let you wear feminine things Lorne?" she asked, positioning and reinforcing the word in his mind. "I?ll let you wear the feminine pretty things from now on," she said pleasuring him. "From now on, you?ll wear the soft things you like, pretty things. You like to feel feminine, to be pretty, and that?s wonderful isn?t it? You like to feel wonderful and you like that I let you, don?t you Lorne." She was stroking him rhythmically and knew it wouldn?t be long before he came. "Yes, I like to feel wonderful." "You like to feel pretty and feminine don?t you Lorne? You like that I will let you wear pretty things," she continued. "Yes, thank you for letting me wear pretty thinks" "You like to look your best, and you like to wear feminine pretty things. You like to wear your hair to make you look more feminine. From now on, you can wear things that make you look beautiful for me. It?s ok and you know I like you to beautiful and pretty for me. Do you like to look beautiful for me Lorne?" "Yes," he whispered back to her. "Yes, that?s right. You don?t want to disappoint me do you Lorne. You want to look your best for me, don?t you?" Lorne shook his head side to side. "I would never want to disappoint you." "It makes you feel proud to look pretty for me. It makes you feel good. When you look pretty you feel more confident don?t you? You know I like it when you?re confident, don?t you. You know I like it when you look beautiful and feminine for me don?t you?" "Yes" "From now on, you?ll want to feel more feminine. You?ll want to look pretty and feminine, because you want to be beautiful. You?ll want to make me proud of you for how good you look. How beautiful you look. Won?t your mother be proud of how beautiful you are? You always wanted to make your mother proud didn?t you Lorne. She would want you to look good, to feel good. You feel good when wear beautiful clothes for me don?t you Lorne?" "Yes, I like to feel good. I want to be beautiful so I can feel good," he gushed, clearly close to orgasm. "That?s right release it all, Lorne. Release all those bad man feelings. It feels good to feel beautiful and you?re going to be beautiful Lorne. You?re very pretty and I like to reward you when you?re pretty don?t I," she said, working his cock. "Yes, you always reward me." "That?s right. Promise me you?ll do all you can to look pretty and beautiful for me. Promise me that you?ll feel really good when you look pretty for me and I?ll reward you." "I promise Anna. I promise I?ll do anything for you," he half whimpered, ready to explode. "I?m going to reward you now because you said you?ll wear soft pretty things for me to look feminine and beautiful and you?ll wear your hair to look pretty. It?s important for you to uphold your promise to me, isn?t it?" He nodded vigorously, the panties still against his face as if frozen there. "That?s a good girl," she said, using the feminine noun, so it was the last thing he heard before she placed her lips over his cock and pumped him to ejaculation. He moaned softly as he unloaded his seed into her mouth, flinching one last time before relaxing back into the couch. Chapter 5 Anna got up early, careful not to wake him. She took one more look at his cock before getting out from under the sheets. It was such a shame it would be shriveling up soon; he had been magnificent last night, but only for one round. Between the fellatio on the couch before dinner and the satisfying intercourse they had when they got upstairs, he wasn?t able to perform anymore that evening. The hormones were slowly eating away at not only his male sex organs but also at his sex drive. She retreated into her massive closet and quickly put on her work out tights over her long lean legs and a sports bra along with a few extra layers to keep her warm on her run. As she came back into the bedroom, she swept up Lorne?s clothes into her arms and left the room, closing the door behind her. She walked down the hall, contemplating what to do with the garments. Her plan was always to slowly start getting rid of the men?s clothes he had brought with him, leaving only what outfits she left him in his closet, but she didn?t want to do it too fast and startle him before the conditioning was set. She decided she would just take the shirts and leave him the rest for now. She had managed to take his measurements after dinner the previous evening so she could start to find items that would fit him. Thankfully he was so scrawny the smaller sizes of women?s clothes would fit him well. His chest and waist were comfortably a size 6 but it was his hips that threw everything off. His hip measurement put him at a size 0. For separates that was no issue, but she?d have to get dresses in a 6 or 8 and then pad his hips and ass to fill out the dress. Better yet, just tailor everything... First things first, she reminded herself. She dropped the clothes back in his room and headed downstairs to get rid of the shirts before heading out on her run. She was back, showered, dressed and sipping her second cup of coffee at her computer when Lorne finally came back into his room naked. She watched him through the camera pause by the clothes she had put on his bed, then walk into the closet. He went to the drawers and opened the top drawer, lingering again in front of it as if debating with himself. Finally, he pulled out a pair of satin panties and carefully stepped into them. Once on, he examined himself in the mirror, spinning side to side, looking from all angles. Lorne studied his torso. He cupped his swollen chest, probably aware now that they were larger than was normal for a young man, the beginnings of more classic female breasts. If they concerned him, he didn?t show it, which was interesting, Anna noted. He should be very concerned that his body was slowly morphing, but she had spent the last three months giving him therapy to cope with this exact situation. Granted, most of the overt stuff was in hypnotic suggestion, but she had spent a lot of time talking with Lorne about his mother and about his own femininity which he didn?t even realize he had until she told him he did. It was unfair manipulation, and she took joy in doing it. But, regardless, it was all part of the plan. Lorne pulled his hands from his breasts and looked down. Anna assumed he was studying his new mammaries but surprised her when he picked at the little hairs on his chest. Soon he was again gazing into the mirror looking at all his body hair. Compared to a lot of men, there was relatively little hair. He had some on his shoulders, his ass and legs, and of course, thick tufts around his genitals. Anna could tell that he was struggling to reconcile the feminine look he was being conditioned to want to see with the reality of the man in the mirror, covered in hair. Soon he turned from the mirror and opened a lower drawer pulling out a pair of boxers which he pulled on over the panties. He then looked around for a while and finally grabbed a black satin robe from the hanging rack and put it on over himself. He closed the front and tied the satin belt just above his left hip. Only his upper chest was visible down to mid-thigh where the robe ended. He looked at himself in the mirror again and, satisfied, walked out of the closet and out of the room. Anna assumed correctly that he would be coming down to the kitchen, so she rose from her desk and quickly walked back to the kitchen to meet him. She filled her coffee cup before turning around and leaning against the counter, as though she had been waiting for him. "Well hello sleepy head," she said casually as he came in. She pushed off the counter and met him in the middle of the room, wrapping her arms around him and kissing him. "Oh, I like the robe on you, darling. It suits you," she said, making a point to look him over. "Thanks, I wasn?t sure if it was meant for me or not, but I didn?t bring a robe." "Perfect. If it fits, wear it I say! Anything you find is yours to wear dear," she said. She pulled into him looking into his eyes as she pushed a bit of his hair back over his right ear. He didn?t have his headband in, and his hair fell languidly down to his shoulders. Smiling, she slid her right hand under the tie and into his robe and before he could protest, had her hand down his boxers. The satin panties seemed to perfectly hold his cock and balls in place. "Oh, a special treat for me, eh? I like surprises!" she gushed, cupping his balls in her hand and pulling him closer to her with her other arm. Lorne not knowing what to say, turned bright red, a pained look on his face. "Mmm...," she coed at him, "that is so sexy. It makes me want to fuck you, Lorne," she added in a sultry tone. She grabbed the back of his head and kissed him hard, making certain to use her tongue liberally. It was all about reinforcement, she thought. She pulled her hand away from his balls and hooked her thumb around the waist band of his boxers. She broke away from the kiss and, dropping down, pulled his boxers swiftly down his legs all the way to the floor, waiting for him to move. Not knowing what else to do, he stepped out of the boxers, thankful his robe was still tied closed at least. She stood back up and twirled the boxers on her fingers. "These belong to me now," she said with a wicked smile. "Get your coffee and come sit with me," she said taking her own coffee cup and walking out back to the great room, boxers in hand. Lorne stood for a moment in shock. He didn?t even really know what just happened. He was now standing in the middle of the kitchen in a woman?s black satin robe with women?s black satin panties on. The reality of that sort of sunk in and he pulled his robe closed as far as it would go before shuffling over to the coffee maker. Soon he padded barefoot into the great room and found Anna in the corner of one of the couches, coffee cup on the small table beside her. She motioned for him to sit right next to her which he did, careful not to spill his own cup of morning sustenance. As he settled in Anna pulled him close so that he leaned back against her, her right arm around him. As they chatted, she lightly stroked his immature bosom through his robe, and they chatted. The sensation drove Lorne wild. His nipples had never been this sensitive before. It was actually quite nice, sitting there that morning they both thought. Soon they had finished their coffee and Anna was ready for the next step in her plan. "Lorne, honey, I?m going to give you a spa treatment now, how would you like that? Just a little welcome to the country house," she said. "I used to work in a spa to help pay for school back in the day," she said remembering back all those years. "I never get to work on anyone so this will be fun for me. What do you say?" "Sure, how could I say now to that?" He said. What else did they have to do today? "Excellent! Oh, this will be so fun. Come on," she said pushing him upright so she could get up. She stood up and offered him her hand to get him off the deep couch. Hand in hand, she pulled him up to his feet and lead him back to the spa room, taking his boxers with her. She led back to the massage room and into the center of the room near the spa table and then spun around facing him. "Now, let?s get you out of the robe and onto the table," she said, grabbing the sash and untying the robe. He tried to protest but she had the front of the robe open and began sliding the robe down the back of his shoulders. It fell to the floor just as quickly. He was completely exposed, just the black panties left on his body and he felt the warm blood start to rush to his checks. Anna didn?t even look at him but spun back, walking around the spa table, which was already made and ready for use. "Up you go, face down please," she commanded, patting the table. Lorne hesitated, wondering what to do about the underwear, but climbed in between the spa sheets, thankful to be covered up again. Anna busied herself turning on the table?s heating coil and turning on the heater to the wax warmer. She pulled down a box of wooden applicators and found another box of waxing strips and latex gloves. She then opened a cabinet down below and removed several bags of hard wax beads as Lorne adjusted the table extension for his face, oblivious to what she had planned for him. It would take twenty minutes or so for the wax to melt fully so she began by giving him a dry massage; Oil would make the waxing harder. She started on the top of his body, pulling the sheet and blanket down so that they rested just above his waist. Once done with the upper torso, she covered him up again and reversed the fold, uncovering his lower half. She took hold of the panties and slowly pulled them down his body. He felt the soft warm fabric slide down his legs, happy she couldn?t see his face as he blushed again. She resumed her massage, working down his legs, finishing at his feet. Thirty minutes had passed and by now, the wax was fully melted and ready. It was time to start the real treatment. "Darling," she said, "I?m going to tidy you up a bit and get rid of all this hair," she said. Funny, he thought, he was just thinking about his body hair this morning. "What did you have in mind, Anna?" he asked, face still buried in the headrest. "Have you ever had a wax, dear?" she asked casually. "Ah, no, why?" "Well, I?m going to give you a full body waxing today I think." She slid her hand down between his legs and under him to his genitals. "I want you clean and bare for me. That would be so sexy, don?t you think," she asked. "I...I don?t know Anna, that will hurt won?t it?" he asked, thinking of the hair ripping from his body. "Well, it won?t be the best feeling no," she said. "But it will be SO worth it when it?s over." She kept her hand where it was but leaned way over to whisper into his ear. "I?ve been looking forward to this. You don?t want to disappoint me do you, honey?" she breathed into his ear. He felt a sudden wave of concern flood over him as his conditioning manifest itself. He didn?t want to disappoint her. "No, no. It?s just...well, I?ve never been waxed before, is all," he said, trying to reassure her. She stood back up. "Wonderful!" she said in a happy tone. "I?ll get started on your back," she continued as though the matter were settled. "How bad could it be," he thought to himself. "It all grows back anyway." Anna spent the better part of three hours prepping his skin and waxing him from neck to toes. He was not that pleased with the "Brazilian" portion of the treatment and made more than a few noises as the hair was removed from his balls and ass crack. His arm pits, too, proved to be sensitive, though he didn?t mind the eyebrows getting plucked and waxed. Admittedly, she had read about, but never performed a Brazilian wax on a man, so she probably wasn?t as adept at is as a professional, but she was pleased with her work when she was done. She took this occasion to examine his genitals as well and they were definitely shrinking from the hormones. Her European contact said that his formula would likely take no more than three months after the second dose to have full effect. From the looks of it, she didn?t doubt that at all. She wondered how long she had. She?d have to go back to her dildo soon. "Now, I?m going to apply some calming cream, which should help with any discomfort." She opened another cabinet and pulled out a tube of soothing cream and another post waxing cream with aloe. She put the soothing cream liberally throughout the Brazilian area and in his armpits. The aloe cream went everywhere else to sooth and clean his skin so he wouldn?t have rashes. Lorne relaxed as she applied the various lotions and could feel them cool his inflamed skin. It was going to be a while before his groin felt better, he knew that. He was secretly happy with the idea of being bald down there though. He had always wondered what it would feel like. "Ok, darling, we?re all done!" she said, removing her gloves. "Here are your boxers, we don?t want anything tight against your skin for a day or two, and I don?t want you to run your hands all over your body either to keep bacteria out of your pores. You can head back upstairs and take a shower but not too hot and not too long as your poor skin needs to heal. If you have any red spots by this afternoon, we can put some antibiotic ointment on them." He sat up and kicked his legs over the side of the table. She came to him and kissed him lightly on the lips. "I?m so proud of you darling. I?m so happy and look at you! You look wonderful!" she said enthusiastically. She handed him his boxers and as he gingerly put them on over his smooth and exposed manhood. He gave a quick shiver as the cool sensation seemed to take hold of him. She retrieved his satin robe and, returning to him, held it out for him to slip his arms into the sleeves, helping it up over his shoulders as he did. The feeling of the robe against his fresh skin was electric, especially on his bare arms and chest. He tied it together and the two left the spa together, Anna to go prepare lunch and Lorne to take a shower. He was careful not to take too long but definitely explored his slick new body. As he stepped out of the shower, he had come to the conclusion that the waxing was much better than he had anticipated. Chapter 6 The next several weeks came and went. They both worked during the day and played at night. Anna kept up the therapy both to reinforce what she had already implanted and to ward off his growing unease at both his behavior and his increasingly androgynous look. At least their time in bed was delicious thanks to his smooth bare skin and his growing breasts. Outside, the world seemed to have been flipped upside down - as Anna had anticipated. New York announced a shut down and shelter-in-place order for everyone. Schools were closed as were all ?non-essential? businesses, including Lorne?s caf?. It was doubtful that job would be waiting for Lorne when they eventually returned to the city. Anna didn?t say anything, but she was fairly certain that the accounting firm would need to tighten its belt as well. She predicted he would be fully unemployed in the coming month. The economic Armageddon was looking like it would add another billion to Anna?s wealth when all was said and done. Oil had already lost almost two-thirds of its price per barrel and that short alone would have made the firm?s year for their investors. While there was a lot going on, she wanted to keep track of, the firm really only had to sit and wait as the destruction of the global economy unfurled and paid them handsomely as it did. It made her giddy to think about. It also allowed her plenty of free time to tend to Lorne?s transformation. Lorne continued to exhibit behavior that implied the suggestions she gave him were taking hold. She watched him through the camera in his room during the days when he thought he was alone. He seemed to have figured out that everything in there would fit him and had been trying the blouses and the occasional skirt on. He simply loved how the garments felt against his nude skin. By now she had gotten him to wear panties exclusively and had purged his drawers of any of his old underwear. As she sat watching him today, he was in the bathroom sitting at the vanity brushing out his hair, nothing on but his panties and a red satin robe open in the front. He had been using the hair regime she told him to, and his long hair was enviously luxurious, soft and shiny like a shampoo commercial. Little shit, she thought to herself. Any woman would kill to have those locks. He finished brushing and this time, instead of putting in the hair band, he parted his hair on one side and brushed it straight as a woman would. Once satisfied he opened the top drawer and pulled out a tube of red lipstick. He leaned into the mirror and applied it to his lips, careful not to color outside the lines. When he was done, he stepped back and examined himself in the mirror. She watched as he reached into his panties and tucked his manhood back between his legs, leaving a satisfying flat front to his panties. He seemed to pose in the mirror satisfied with his feminine look. Anna beamed at her screen. She loved winning. Everything she had done in the last four months was winning and she was determined to keep it that way. By April, it was time to enter the final phase of her plan. Anna had been replacing his clothes slowly over time, at first with either more feminine looking men?s clothes or women?s versions of the garment. For example, all of Lorne?s jeans were switched to accommodate both his growing derriere and to fit more in a women?s style. His t-shirts were no longer a size too big for him but were cut for a woman?s body and his sweaters where softer and in brighter colors. Lorne was clearly aware that something was going on with him and they spent more and more of their "therapy" sessions working on what Anna felt was shaping into a form of gender dysphoria. He told her that what had started out as a sort of trippy sexual fetish for him was increasingly becoming all he could think about. Plus, his body was definitely changing. The mounds on his chest could not be explained away and his hips and ass were rounded, despite the heavy cardio work outs and sensible diets they were both working on. Anna had to admit, he looked good. His waist was taught and besides his softer thighs, his legs were long and lean, very shapely. She had designed their workout with her personal trainer to not touch his upper body lest he put on muscle mass. Instead she only had him stretch and lightly tone with some yoga moves and the effect were nice, thin, lean arms. Anna had prepared for this period by giving Lorne suggestions that he had always desired to be female and that this was due in large part to his attachment to a strong female, his mother. For weeks she had introduced this notion so that she could have an open, conscious conversation with him and get him to come to the "realization" that he wanted to explore his feminine nature. It was probably the most difficult part of this whole plot and it had to be done perfectly or risk complete failure. Lorne had to think that these were feelings that were deep inside of him and were just being unearthed, likely as a response to the world?s upheaval due to the pandemic. If she could get him to accept that premise, then she was all but assured of victory. For some reason, though he had never participated in therapy before, Lorne really enjoyed their sessions and felt incredibly blessed that he had a world class therapist all to himself. As such, he was an active participant in the sessions which they usually had in the late afternoon after the markets closed so Anna could focus. "Ok. There is something I need to talk to you about and haven?t been able to up to this point," he started. "There is just something really odd going on here Anna, and I need to understand what it is. I?ve tried to figure it out myself, but I just can?t anymore, I just don?t understand what?s happening to me," he started. "Well, that is a big admission, Lorne. Thank you for trusting me enough to talk with me. Tell me more, what exactly is troubling you?" "I can?t stop thinking about myself...I mean, my body, I guess," he paused, searching for the words and Anna let the silence fill the room. It was important he say it. He started again. "I keep looking at myself in the mirror. At first, I wasn?t sure if I liked the waxing, I mean, I was totally nude and bald. But then...well, I figured out I really liked it. I really liked not having hair on my body and feeling smooth and clean. And my hair," he said, motioning to his glistening soft hair that fell around his shoulders. "I began to like how it looked brushed out like this...And then, with all the clothes in the closet...I like the soft and pretty things in there," he said, using the words she had put into his subconscious over these last weeks. He stopped, clearly struggling with what to say. He was wringing his hands nervously and he couldn?t make eye contact with her. "I started just trying different things on, just for fun, you know? But... I looked really good in some of the things...and it felt really good and it got... I don?t know, really confusing for me. I felt like I should stop but I didn?t want to, you know?" he asked, looking up at her hoping for reassurance. "Lorne, how long have you been struggling with your desire to be a woman?" she asked softly. The pulse in her neck quicken. The game was on the line and she would need to play her hand carefully. "I...don?t... think... I have?" he said, drawing out the words as they came to him, not sure of himself. "Wait, have I?" She let the words linger in the air. It was important he say it. Lorne was lost in thought, searching his feelings "I don?t know..." he said finally. "Maybe I do, Anna. Oh my god! Maybe I do want to be a woman," he said more hurriedly, clearly worried. "Lorne, there is absolutely nothing wrong with these thoughts. You needn?t worry. Just take a breath and tell me more," she said calmly, reassuringly. "It?s just, I never had these thoughts until I met you. And...my body," he said looking down at himself and the cute, soft designer black turtleneck sweater he had on. His hair was pulled to one side over his shoulder and he looked like he had just jumped out of a Ralph Lauren catalog. "Tell me about your body, Lorne." "It?s changed. Obviously, its fully changed, Anna. I mean look at it," he said standing up from the couch and slowly turning around. "My ass is bigger for sure, I have...breasts, I think, and there?s something wrong with my penis. It just doesn?t work like it should," he said, slowly sitting back down again. "I?ve tried so hard to keep making love to you, but I just can?t always get it, you know...going. Get it hard..." he paused, a little defeated. He wasn?t ashamed that he couldn?t get his dick to work, it?s just that he didn?t like feeling like he let Anna down. He felt guilty, exactly how she wanted him to feel. "You needn?t worry about me, darling, I?ve been enjoying our time together thoroughly." He still looked pained, like he had more things to say. Anna knew there would be a time when he accused her of putting him through this. There was no way to avoid that and follow through to the end. He was not an elite academic like she was, but he was no dummy either. She braced herself for what she knew was coming and remembered that she had planned and rehearsed for this moment. "I just...," he started, unsure of how to say what he needed to say. "I mean, that is...you?ve been so good to me out here and I?ve loved being here with you. Who knows what would happen to me if I was stuck in Manhattan...? It?s just, well..." his face flushed as he grappled with what to say. Better to just come out with it he decided. "Did you do something to me, I mean, to my body," he motioned to himself with both hands. "Because, nothing else makes sense to me. I mean, nothing else can explain this...this!" he said emphatically, again gesturing to himself. He looked up at Anna, hoping she would have something to help explain just what the hell was going on. Anna took a deep breath and started. "Lorne," she paused to add effect. "There has been a lot going on in our lives, in our world really. You?ve been uprooted from your home and brought out here. As comfortable as it is, it?s not your place. There is an innate biological response to the things we experience. For example, have you ever found it difficult to defecate somewhere besides your work or home? That is actually a biological defense hardwired into us to help us protect ourselves when we are in unfamiliar surroundings. Everything about your world is unfamiliar right now and it does not surprise me that this has brought on long suppressed feelings." She paused to let him wonder just what his long-suppressed feeling might be. "It is actually a natural response to some pretty strong stress you?ve had in your life lately. You?re likely experiencing the beginnings of gender dysphoria brought on by acute stress load." "What is that exactly?" Lorne asked a little concerned. "Well that is simply a struggle one has between a their physical or assigned gender and the gender with which they identify or want to identify. You are finally in a place, a safe place, here where you can explore this issue, even if just subconsciously, and it is manifesting itself. Likely, the physical changes are associated with this conflict you?re having as well. Your body is letting you know that it?s alright, that it is ready to take the form you?re so interested in having." She let that sit. If he accepted this, she could push forward. If not, if he called ?bullshit? as it where, then she?d have to really fight hard to keep her experiment going. She didn?t want to have to explain any more about the physical changes as they?d be hard to defend if he started pushing. I simple google search would likely punch some big holes in this lie. Better to leave it as some sort of nebulous ?your body is responding to stress? bullshit she thought. "But where does this come from, Anna? I?ve never thought about being a woman before. I mean, that?s what you?re saying right, that I somehow have decided I want to be a woman?" he asked. Tears started to form in his eyes. "Hormones are bitch aren?t they buddy," she thought to herself. "I?m not saying that, Lorne. You just did. This isn?t about me at all, it?s about what you want. I?m only trying to paint around the edges and help you work through what you?ve been thinking and feeling all along. Why do you think you want to be a woman?" she asked careful to frame the question as if it were a fact. They spent another hour working through the issue and she let Lorne fill in the gaps for himself. Ultimately, he came to the conclusion that his mother had always wanted a girl and that he had repressed this information. Now that she was gone, he felt guilty for not having given her what she wanted and so he was somehow cathartically manifesting his guilt into a physical and mental shift to femininity. God it was easy to manipulate people, she thought. She didn?t even have to use any pharmacological help to get him to come to these conclusions. It was such psych-babble bullshit, but man, do people eat that shit up when you served it to them. Regardless, he was hers now, utterly. She almost felt sorry for him accept she was so thrilled with herself that she could see the light and the end of the tunnel the emotion escaped her. Between this and the insane amount of money she was making in the hedge fund as the world crumbled, she figured it was time to celebrate. "Lorne, you?ve done so well today. I?m so proud of you, honey. Come here and give me a hug," she said standing up. Lorne stood up and the two embraced and she kissed him. "Now, let?s celebrate this moment and then let?s go upstairs and change for dinner." He didn?t know exactly what she meant by that, but he could definitely use a drink right about now. She went behind the bar at the far side of the great room nearest the kitchen, to the wine fridge and pulled out a bottle of expensive sparkling wine from Italy. Soon she had the bottle opened and poured the bubbling contents into two glasses. "To you and your bravery, dear. I?m really very impressed with how you?ve opened up about this," she said. They clinked glasses and each too a big sip. She topped off their glasses again and then took Lorne by the hand. "Come, it?s time we let you take the next step," she said and, glasses in hand, led him upstairs. He wasn?t sure what they were going to do but he was getting excited. Instead of turning to her room, they instead walked to his room and into his large closet. When the lights went on, it showcased the fact that there were considerably more clothes hanging in the closet now than when he had arrived weeks earlier, perhaps twice as many, though the closet was nowhere near full. She had been telling him all along that she?d be ordering him things as she saw them and a steady stream of packages and deliveries had been coming to them almost from the start. Maybe he didn?t want to know that she was complicit in all of this, but at some level it was clear that this wasn?t really a wardrobe made for a man. Maybe his subconscious didn?t want to let him believe that she was putting women?s clothes into his closet for him to wear, because if it did, not much of what she had said downstairs would have made sense. She had been sort of dismissive about the things she bought him, saying only that she thought he?d look good in these items and so had gotten them for him. She never really elaborated beyond that. She had been correct in her diagnosis months earlier that his naivety would never let him believe she was controlling him. On top of that, the conditioning she?d given him made it that much harder for him to accuse her any more than he already had. "Take off your clothes honey. Let me pick something out for you," she said. His heart started to beat a bit faster and he was strangely excited by the fact that she was now an active participant in what he had thought was a hidden fetish. Anna went to the rack and started perusing through the clothes while Lorne started to undress. She pulled a few things off the rack and examined them then, rejecting them, returned them to their perch. She finally came upon the soft purple, almost lavender satin wrap blouse she had seen him try on before. This would be the one to start with she thought, along with the black bandage pencil skirt. She pulled the two items off the rack and hung them on a hook off one of the built ins. "Yes, I think those will do," she said then went over to the drawers. She opened the top drawer and rooted around. He had made a bit of a mess of the drawer in the last weeks, but she managed to find stockings, a white satin and lace bralette, panties and a white garter belt that all matched. She turned around and handed them to Lorne who was now in only panties. She said nothing but motioned to a small cushioned stool for him to use as he put on the thigh high stockings. She helped him bunch up the stocking so that the toe was just inside the opening and let him slip his foot in, pulling the stocking up his now smooth legs to its full height. He did the same with the second stocking and stood back up. He took off the pair of panties he had on and replaced them with the white ones. She put the garter belt around him and fastened it behind him leaving the little decorative rose in the front. She then had him thread the garter straps under his panties so he could get them off without pulling down the garter belt as well and helped him fasten them to the tops of the stockings. She placed him in front of the mirror and brought the satin bralette around his front for him to put his arms through. She pulled it around him and flush to his skin so that the satin triangles of the bra neatly fit over his budding breasts and areole. She fastened the back and fitted the straps for him. They both looked as his reflections silently in the mirror. Both were becoming aroused but now was no time to attack one another. Next she pulled the skirt off the clip hanger and held it out for him to step into. She pulled it up over his slim hips and the bandage material stretched around him. It was high wasted and made stretch material, so it clung nicely to his shape showing off his tiny hips in a way other skirts couldn?t. Finally, she removed the wrap blouse from its hanger and held it out for him to put on. He pulled it up over his shoulders and she helped him wrap around the two ends and tie them off over his left hip. The shawl collar came together with a nice "V" shape just above where the bralette would show. Frankly, he didn?t need the bra, but she wanted him to feel it on his chest and around his torso as a visceral reminder. "Pick some shoes, dear" Lorne went over to the shoe rack and was about to pick a pair of black flats. "No, no, the heels, darling. You want heels with that skirt, trust me," she said. He took out the black patent leather shoes and slipped them on his feet, bringing the ankle straps around and closing them. He stood to his full height and could feel both his calf muscles and his ass respond to the angle of the shoe. He walked back over to the mirror, careful not to roll his ankle. He was nervous and excited in one. Anna came around behind him and gave the outfit a few tugs here and there and proclaimed it perfect. She reached back over to the chest of drawers and retrieved their drinks. She again gave him a "cheers" and clinked their classes. He came close to her, pulling her in and kissed her, tenderly, but fully. "Mmm," she replied breaking away and taking another sip of the wine. "But we?re not done yet my love." By now it was early evening and so she took out her phone and texted Andrew about what time she wanted dinner served (they were still getting ready she told him) and then again took him by the hand and walked him in the bathroom. She pulled out the vanity stool for him and had him sit in front of the mirror. First, she brushed out his hair again and styled it with a flat iron. As she worked his hair, she explained how to do each step and also gave him tips on how to style his hair using the various products. She explained the again the shampoos and conditioners, then the essential oils, the mouse, the gel, the sprays and serums. There was a lot to take in. When she had it styled in a very chic straighten look, she pulled out the make-up and did up his face, again explaining everything as she went. His soft features meant she didn?t have to hide anything with foundation, but she made his whole face up expertly, doing a heavy eye and minimal lip to accent his new hairdo. As a final step, she fished out a pair of faux diamond earrings and he put them in to his ears finishing the look. She also grabbed the perfume bottle, one of her favorite scents, and had him hold out his wrists so she could dab some of it on him. A pleasant citrusy floral scent filled the room and his nostrils. "Now, come with me to my room while I get ready." Anna first chose a tailored blue body suit that looked like buttoned down dress shirt, complete with white French cuffs. Then she combined it with a sharp pair of black slacks with a black leather and silver buckled belt. The body suit hugged her frame and made it so no matter what she did, the shirt part would never become untucked and lose its fresh, crisp lines. Finally, she accessorized with a yellow silk tie with a wide Balthus knot, dark grey vest and four-inch Louboutin heel. She pulled her hair back in a ponytail she clipped into place with a grand Yvette tortoise shell clip. To finish her look, she did light make up with a dark read lip and then accessorized with a pair of stunning drop diamond earrings. "What do you think darling," she said looking into the large mirror. "we make quite the couple, don?t we?" She brought Lorne into the bedroom and hugged him again. "Now, since we?re really the only ones here, and will be for some time thanks to the quarantine, I think we should explore your feminine side as much as we can. I?d like for you to spend the next several weeks dressed as a woman, sort of get used to it and see what you think. This will be a good way to explore your feelings and find out what you really want. I?ll be here with you and support you. We?ll have such fun you and I!" Lorne should have guessed this was coming but even still, he had a rush of excitement prompted from the many sessions of hypnosis. It was as though a weight was lifted and he was now allowed to openly do something he had been repressing. He started to cry tears of...well, he guessed joy. He was incredibly emotional at having the opportunity to now openly wear the items he was coveting in the closet. "Oh, darling," she said in a soothing tone coming to him with a hug. "No need to cry, dear. We?ll get you sorted. I?ll tell you what, we?ll pick out some clothes you like tomorrow, eh? There, there," she said trying to sooth him as he openly wept. She was glad she?d chosen the waterproof mascara. Once he?d had his cry, she freshened him up and they headed downstairs. One surprise was how well he moved in his heels. He didn?t even so much as stumble. They went straight back to the bar and filled their glasses again to the brim with the lovely sparkling wine, drinking half the glass each in the first go. Andrew sat them at the farm table and brought them three wonderful courses and then a light desert, never saying a word about the new "miss" in the house. As for Lorne, he was surprised at not only how much fun he was having and how good he felt, but that he wasn?t embarrassed in the slightest. He wasn?t sure if he should be concerned or delighted so he just went with it. "There, I?ve just texted my hair lady. For a few extra shekels, she will gladly come over and do our hair tomorrow. Didn?t I tell you how wonderful it was when they come to you?" she said. "God, I love my life," she said under breath taking a long sip of wine. Chapter 7 Lorne awoke in Anna?s bed in a pink satin chemise with black lace accents. She had shown him how to take his make-up off before they?d gone to bed to make love. Lorne had really struggled to get an erection and when he did finally ejaculate, there wasn?t much to it he didn?t think, though it was satisfying. He thus spent a lot of time using his tongue and fingers, trying to be a generous lover. Anna told him to get something comfy on and to meet her in the spa. He needed to be waxed again. Thankfully, having taken good care of his skin and exfoliating as he should, and because the hair was finer and less course, the waxing wasn?t nearly as bad as the first time. It still wasn?t pleasant, but it went a lot faster. They again put on a post wax skin regimen and he put on some loose clothing. They had just finished lunch and were sipping tea again when the hair stylist showed up. They returned to the spa room, this time on the "salon" side. Lorne?s hair was a sandy brown and Anna wanted to lighten up the color. The stylist and she spent some time talking as though Lorne weren?t there and decided to add golden blonde highlights. First, she cut the hair, layering it and making sure to get any split ends taken care of. She spent the next two and a half hours highlighting his hair before finally it was Anna?s turn in the chair. Lorne hurried upstairs and into his closet so he could try some of the dresses that were hanging in his closet. It was as though his new hairdo steeled him against the shame of wearing them. He chose a nice lined shift dress and tried it on. He looked fabulous, if he did say so himself and couldn?t wait to show Anna! First, though, he doffed the dress and took the time to put on a bra and pantyhose and picked out a low heel to wear. He went into the bathroom and put on mascara, a little blush and a nice pink lip gloss. He got out some silver dangling earring and put those as well. He had seen a cashmere wrap in her closet so went down the hall and into her expansive master suite to retrieve it and a few silver bracelets. He then went back down to the great room to read and wait for Anna. Andrew was a dear and even brought him some tea. "I love that dress on you, Lorne," Andrew said as he brought in the tea. "I just had to tell you that and your hair is gorgeous. Do you just feel fierce or what?" he said encouragingly. Again, Lorne started to tear up at the sweet gesture Andrew was giving him. "Oh, Andrew, thank you so much. I?m sorry...it?s so sweet of you to say it?s making me cry. I can?t seem to help myself these days," he said, fanning his face. "Honey, don?t even worry about it," he said. "Anna is going to love this look! Now, just holler if you need anything else girl," he said then headed back to the kitchen for some dinner prep. Anna came out, finally, chatting with her stylist. They stopped in the great room and soon Andrew was walking the stylist out. Anna came around to Lorne. "I love that look, Lorne!" she gushed. "How do you feel, do you love the hair? I love the hair!" "Thank you, Anna. I do love it, I think," he said honestly, running his hand through it. Anna sat down next to him. "I?ve been thinking, honey. I?m worried for your accounting firm and if they can weather the pandemic or not. I know you aren?t that happy there anyway so why don?t you come work for me? We?ve decided to promote Angelica to a junior analyst role, so I need a new assistant. I can use the extra help in keeping things in order and it will be so much better to have someone here with me. I can?t handle having to email or video conference my assistant every time I need something. What do you say, hmm? We can try it out for a while or until you find something else. Plus," she paused, giving him a sultry look, "I can provide perks most employers won?t...". She paired a wicked grin with a little wink. "That would certainly be a relief because I think you?re right. I was already getting signals from them they would be tightening their belts. If I left, it might help them keep the other staff on a little longer," he said. "Excellent. You can start on Monday. Also, since you?ve been telling me all this time I need to upgrade my art collection here at the house, your first task will be to find me the pieces I need. We?ll have quite a war chest to play with given how well we?re doing in the market right now. It should be a future art gallery owners dream don?t you think?" "That would be amazing, Anna! Thank you," Lorne said excitedly. "We?ll, that?s not all. Did I mention there was a signing bonus?" she said, sliding over to him and kissing him. Chapter 8 In preparation for the following Monday?s start date, they had come to a set of understandings. Along with the typical tasks and job requirements, they agreed that Lorne was to wear feminine, office appropriate attire while on the job. That meant skirts, blouses, and heels, but Anna was insistent that Lorne think about what he would have to wear if he was in an actual New York hedge fund office representing her. She was to have not only the clothes but the accessories, make-up and hair one would expect of a partner?s personal assistant. Second, it was time to fully adopt his female persona, if he was to understand what he wanted for himself, just while they were in lock- down. From that point forward "he and him" would be "she and her" and she would use the name Lauren. He would also start vocal training lessons right away with wonderful speech language pathologist Anna knew from her days in practice. In preparation for her first day at work the two had spent much of the previous week shopping until Lauren had a dozen new outfits and dresses, an equal number of shoes, earrings and jewelry, belts, scarfs, a few hats, new lingerie, and summer casual attire. Most important, Anna had said, was to get Lauren breast and hip forms to fill out her figure and accentuate her feminine curves. Anna was so excited to shop she even got Lauren some evening dresses, proper women?s workout clothes and a handful of bikinis for the pool, which she hoped to open soon as the weather turned. It was so much that Lauren had to print off the "looks" from the web pages, so she knew what item went with which outfit. And so, Lauren entered her new office and took her seat at the empty glass desk just outside Anna?s inner office. It was an odd layout for a home office to have space for an assistant, but it worked perfectly for Lauren and Anna. Anna had made a point to inspect the outfit and her look over breakfast but she had passed the test in a fitted white button down bodysuit with a midi length soft gray pull on skirt with ruching, a black leather belt with matching four inch heels, gold hope earrings and a gold bracelet. She had on a strong red lip that fit her warm skin tone, but the rest of her makeup was understated for the "office". By the beginning of May it was clear that Lauren?s body had succumbed to the massive doses of hormones Anna had given him. His genitals were perhaps half the size they had once been, and he had not been that big to begin with. They had receded so much Anna insisted he start wearing thong underwear since he couldn?t fall out of them anyway. Even with the thongs on, the tell-tale bulge was minimal and with some simple tucking, there was no evidence that Lauren had ever had a cock between her legs. This meant, of course that their former sex life was drastically changed. Anna had spent most of April conditioning him to think of penetration as a sexually gratifying act to be done to him. She also spent a lot of time talking to him about his desire for the male penis, fellatio and generally being with a man. Inculcating this desire didn?t turn out to be as difficult as she anticipated as Lauren had from the start been very open to sexual experimentation and new experiences. Finally, she was doing all she could to be dominating to her and to build her subservience toward Anna. One day after a particularly good call with a west coast tech firm, she called Lauren into her office. "We just added another $100 million in profit this year, baby! Fuck Leo, I?M the king of the world! You know what this calls for?" she asked Lauren standing in front of the desk. "What?s that?" she said cheerfully. Anna stood up and undid the front of her designer slacks, then pointed to her silk pantie clad crotch. "This calls for you giving me head. Come here baby and give mama some love!" The look on Anna?s face meant she wasn?t kidding. Lauren blushed, but it had been at least a week since they had been together, and she wanted to make Anna happy. She started to move around the desk. "That?s right baby, come over here and get on your knees and show me what you can do," said Anna purposefully choosing her words to sound crude. Lauren pulled the hem of her cream-colored wool skirt up and bent down from the knee until she was low enough to drop to her knees. Anna had already sat back down, slacks around her ankles, legs splayed to give Lauren maximum access. Lauren reached forward and pulled Anna?s silk and lace panties down her legs, the aroma of her now hot sex permeating her nostrils. Anna was very aroused by the power she was able to exert on her test subject. Lauren leaned forward preparing to kiss her lovers warm snatch. "Not yet," Anna said. "You don?t have any lipstick on. My girls should have lipstick on before they go down on me" Anna reached over to the desk and retrieved her own lip color, handing it to Lauren. Lauren opened the tube and using the metallic top as a mirror expertly applied a fresh coat of pigment to her lips. She looked up at Anna who gave an approving nod. Lauren replaced the top, handed the tube back to Anna and proceed to slowly lick her way into Anna dripping wet sex, careful to lick up every drop of her lovely nectar. "Oh," moaned Anna. "That?s a good girl. Harder baby...that?s right. Mmmm...make me cum" Lauren worked her mouth and head in Anna?s groin until she could no longer feel her tongue. She retreated, sitting back on her ankles just after Anna had climaxed again. The fresh lipstick was now a red shadow around her lips and chin and her hair was disheveled from Anna?s hands holding her face tight against her sex. "Oh god you?re good at that," Anna exclaimed. "I knew I hired the right girl." Lauren sat there while Anna took another moment to bask in her post orgasmic glow. Soon enough she pulled up her panties, then stood and pulled up her slacks, refastening them in the front. She reached across the desk and grabbed a tissue, handing it to Lauren still kneeling in front of her. "You can get cleaned up now, honey. Why don?t you have Andrew get us some tea while you do." Lauren got to her feet, careful not to step on the hem of her skirt or fall over in her heels. She straightened her skirt and re-tucked her satin blouse and headed for the door. "Oh, and don?t think I have forgotten about you. We?ll have a session at five," she said checking her watch. "Of course," Lauren responded. She liked the sessions. At exactly five PM, Anna walked out of her glass office to Lauren?s desk and said, "come with me." Lauren stood up and followed Anna out, but instead of heading to the couch in the great room where they normally had their sessions, Anna instead walked purposefully to her bedroom. Once there, she told Lauren to strip. She went into her closet and after a couple of minutes came back out wearing a long silk robe tied at the waist and carrying a box from a designer boutique and a pair of silk stockings. "Put these on," Anna said, handing her only the stockings. She went to the bed and sat down with the box on her lap waiting for Lauren to finish. "Underwear too please," Anna said when Lauren had gotten down to just her thong. Lauren complied and dropped the underwear to the floor before rolling down the stocking and deftly rolling it up her leg as she balanced on the other foot. She did the same on the other leg and soon stood up. "Put your heels back on now, please," Anna said as she stood up from the bed. She turned around and placed the box on the bed, opening it as she did. She pulled the delicate tissue paper aside and pulled out the contents of the box, a lovely deep red satin corset with brocade stitching and a heavy busk. Anna expertly loosened the laces in the back and then turned, holding it out for Lauren. Lauren walked to her and turn her back to let Anna wrap the beautiful construction around her. "Arms up dear," Anna said, and Lauren did as she was told, lengthening her torso. Anna came around and soon the heavy metal closures clicked into place in the front. Anna spun her around and began tightening the laces in the back until she was securely in the corset?s grip. Anna turned her around again and saw that her small A cup breasts were nicely held in place, giving just a hint of a d?colletage. "You can begin clipping the garter straps to the stockings, honey," Anna said, returning to the box on the bed. She removed a matching thong but left it there. When Lauren had all the straps connected to the top of the stockings, Anna led her back into the closet to look in the mirror. She had lost close to 3 inches in her waist and the affect was stunning. Even her hips looked bigger, much closer to the proportions a woman would have. "Much better," Anna said. She brought Lauren in and kissed her deeply and fervently. She kissed Lauren until she flushed, only pulling away when she felt she had Lauren?s blood flowing. "Now Lauren, I told you I hadn?t forgotten about you," Anna said still up close to her. "It?s time you learn the exquisite feeling of when a man comes from behind you," she said rapturously as she placed her body firmly against Laurens. "...and takes you. What its truly like to be fucked," she growled. Her right hand went into her robe pocket and produced a dildo. Lauren realizing what it was, flushed red, suddenly both very nervous and very turned on. She hadn?t had much desire these last couple weeks but for some reason, when she saw the fake cock there in front of her, she felt very sexual again. Anna dropped her robe. She had nothing on save her panties and the dildo?s harness on over top of those. Lauren watched as Anna brought the dildo down to the harness and clicked it into place, its long shaft now protruding oddly from Anna?s loins. "Go back to the bed and lean over for me," she said opening another drawer in the closet. Lauren did as she was told, and the nervousness started to show in her hot pink face. She got to the bed and Anna was right behind her. She pushed Lauren over so that she bent at the waist. First, she caressed Lauren?s now wider ass, grabbing it then playfully slapping it. Then she opened the tube of KY jelly she had brought from the closet putting a dab on the first two fingers of her right hand and spreading it deep within her ass checks, right against her anus. Next the coated the tip of the dildo with just enough so that it wouldn?t drip on her rugs or bed spread. She took a step closer and lined up the tip of the cock with the hole that would swallow it, pausing to taunt her. "I?m going to fuck you now, Lauren, like a girl like you likes to be fucked." Slowly, she pushed forward, penetrating her delicious ass. "Relax, darling. Take the cock in and enjoy it." Lauren, arms spread on the bed in front of her, ass in the air, relaxed her sphincter as best she could. She knew she should be horrified, that she should not allow Anna to do this, but she couldn?t help herself. She?d been fantasizing about this for weeks, though she wasn?t sure why. She could feel the tip of the dildo pass her anus and continue up, then back, then slowly up again lubricating her as it moved. It felt uncomfortable, so wrong, so invasive and yet she wanted more. She wanted Anna to fuck her. She wanted to be fucked. She wanted to be a woman. She just hoped she?d like taking a man this way. Soon the dildo was all the way in and gently rubbing against her prostate. It was odd being filled like this but slowly, steadily, she was able to relax and take in the cock. It began to feel good and she was relieved. "How is that darling," Anna said slowly pumping back and forth, her strong hands on either of Lauren?s hips pulling and pushing opposite her thrusts, not letting Lauren get away. "Its...good.... Please, go...faster." Anna picked up the cadence, in, then back, in, then back, in, then back slowly speeding up. Lauren let out a soft grunt each time she thrust the cock into her. She was now fully relaxed and focusing on the foreign sensation, the delightfully foreign sensation of being filled up by a dick. Anna was now pumping rather quickly, and her thighs started to hit with a satisfying "smacking" sound against her ass. Lauren?s own cock stiffened...sort of, and she felt a twinge in her groin. She pulled her head up and arched her back taking all of the thrusts, taking in all of the cock. She started to moan, "oh, yes. Oh, yes, oh..." she bit her ruby lip as she felt the beginnings of her own pathetic orgasm start in her loins. "Faster Anna, oh... Faster, please," she cried out, begging to get to climax. Anna thrust faster, careful not to hurt Lauren and beginning to get quite an abdominal work out. "You like being my little bitch, don?t you? Hmm...?" "Yes! oh!! Yes! Ah...oh my god," Lauren cried out. Those little words sending her over the edge. She quickly brought her hand to her own genitals and caught her orgasm in her hand. Anna slowed her pumping as Lauren twitched and spurted out what little cum she could. Well, at least we know she likes it up the ass, Anna thought. Maybe I could make a sex slave after all. Anna pulled out of Lauren and grabbed a tissue from the nightstand. A quick look at Lauren?s hand told her there wasn?t much to clean up. It was fascinating what the drugs dis to her system she thought as she removed the phallus and put her robe back on, walking back into the closet. Lauren cleaned of her hand and got another tissue to make sure no KY Jelly was still on her ass and lay back on the bed. The corset felt suddenly tight against her. "Darling," Anna called out. "Put the matching thong on and come into the closet please," she commanded. Lauren rolled off the bed since she couldn?t sit up with the corset on and walked to the end of the bed. She stepped into the thong, pulling it up and over her little dingy. She walked in the closet and Anna handed her a long shapewear slip. "Put that on over your corset so you?ll have smooth lines." Lauren donned the slip and once down, Anna closed in and kissed her again fully and passionately. "I told you I wouldn?t forget about you. I wanted to be the first one to fuck you properly. Isn?t in marvelous?" she asked. "I have to it admit, it was much better than I thought. I can?t believe it made me cum," she said, remembering the felling of it pumping into her. "Well, now for the glamourous part of the evening." Anna turned and pulled a long hanging bag from the closet rack. She held it up and unzipped it revealing a beautiful vintage style pink gown. Anna pulled it out revealing a silk satin shirt dress with a full A-line skirt and a button up front. The sleeves were three- quarter length and folded back for a cute cuff. The collar was stiffer like a dress shirt and could be worn up or down. There was a wide belt made of the same silk fabric of the dress that buckled in the front around the waist and would accentuate the hourglass shape the corset created. The look was a throwback to the 1950?s but, as the label would confirm, from a current high-end fashion house. Anna had clearly planned this down to the two breast forms she materialized to enhance her bust. "A present. You should feel like a princess after a good fucking like that." "Oh, my god...Anna, it?s gorgeous. Will it actually fit me? It looks tiny. How did you ever get this here? Anna hung the dress on a peg and spoke over her shoulder. "Not to worry dear. The corset should help, and the top portion of the dress has more space then it seems. The belt will gather any extra for a nice clean fit. That is why we put this all on before we eat! Now here," she said, turning and stepping to a back corner of the closet where she produced a crinoline skirt. "let?s get you into it, starting with this to fill out the skirt" She handed Lauren the crinoline then turned back to the dress swiftly unbuttoned the front. She waited for Lauren to finish pulling up the crinoline then held up the dress to Lauren to wriggle into, carefully. She then helped pull it down and over her body over the full crinoline skirt which made the dress?s skirt full and flared. "Now, do that up and fix your hair so I can go get a drink with my gal!" Anna said. Lauren retreated down the long hall, fastening buttons as she went back to her own room and to the bathroom where she brushed out and styled her hair, clipping one side back. She sat down, feeling again the aftermath of the penetration she?d just had and applied her makeup. She took her time and tried to do all the things Anna had shown her without getting too fancy and messing it all up. She?d been practicing her eyes for weeks and was able to do a nice smoky look with a soft pink rouge and a light pink lip shade that went well with the dress. Before she was done Anna met her in the bathroom. "Well done, you?re really getting the hang of that darling. Here are some pink diamond earrings to go with that dress," she said, her heels clicking on the tile as she walked in. She was wearing a tuxedo outfit. The jacket was cleverly corseted as well, and she wore it with no shirt. The "V" neck plunged down her front hinting at her bosoms behind the fabric. There was a classic style cummerbund and then a feminine take on the tuxedo trousers, still with the satin ribbon down the leg but the legs tapered in down to the ankle. She once again wore her black Louboutin?s with fierce triangular toes and an impossible stiletto heel. She had dark sinister sexy eyes, just a hint of blush and a blood red lip. Finally, her hair was pulled back into a tight ponytail and she wore large diamond earrings, the only jewelry she had on. "Shall we get that drink?" The rest of the night was lovely, and Anna was impressed with the progress she had made with Lauren. She not only had she become adept at modulating her voice to something closer to a woman?s range, but she almost never slipped anymore. Further, her movements and gestures were far more considerate and feminine. But for a few telltale signs, an Adam?s apple for example, there were moments when Lauren appeared to be a real woman. Anna had made every attempt to expose Lauren to a more masculine fa?ade from her; she would have to understand how to react as a woman in a male dominated world. But, try as she might, the best she could do is give but a hint of what it was like. She wore menswear inspired clothes often but that wasn?t the same thing and so she knew it was time to move to the next and final phase. She?d need to make a call. Chapter 9 About a week after the dildo night, as Lauren had come to think of it, they had an early dinner, light and not very filling. Anna then sent Lauren up to her room, blessedly with a healthy pour of top shelf scotch and a set of instructions. The first was to reapply her make up fully, but tastefully and to gently curl her hair. The second was to put on the outfit in the box on her bed and wait. She was to be ready at exactly 8pm. Lauren had grown to love the surprises in the boxes and hoped this one would be on par with the others. She didn?t want to ruin the surprise and so quickly undressed down to her panties in the closet before heading into the bathroom to prepare. She began by lightly curling the ends of her long hair with the curling iron Anna had shown her how to use. Next, she touched up her makeup, making sure to put a heavy layer of the deep red lipstick Anna loved. Once done she retreated back to the bedroom to open the box. Inside, under the delicate tissue paper she found a note and the loveliest piece of lingerie she?d ever seen. She picked up the garment which revealed itself to be an exquisite silk and mesh body suit with long full silk sleeves in a deep rich pink tone. The entire top front of the garment was in this deep pink silk and had a long d?collet? cut from neck to sternum while the entire back was black mesh. At the midriff in the front, it transitioned to this black mesh that ran down to her hips around the derriere and between the legs where there was snap closure. The front had exquisite stitching in the mesh that would conceal her private bits, but the rest of the mesh showed through to her soft creamy skin. Finally, the billowing sleeves came in at the wrist with silk satin ties in a rose- pink color and were perfectly tied in bows. The neck closed around with a gorgeous and soft line of large flowers made of the same rose- pink silk satin and clasped in the back at the nape of the neck. She lay the body suit on the bed and read the note. "A special surprise for you for our big night. Accompany with stockings and black heels ? A" Lauren couldn?t help but grin. She and Anna had not been sleeping together very much anymore now that Lauren had been afflicted with non-functioning genitals. Perhaps tonight would rekindle their lost love making. She retrieved the heels and stockings and returned to bed to don her new outfit. Once on she carefully snapped the snaps in the crotch and attached the delicate straps to her stockings. She slipped on her high heels and went to the mirror to make sure all was right. She looked damn good if she did say so herself. She twirled and looked at her soft rounded ass in the black mesh. "Very fuckable" she thought. She spent the last ten minutes pacing the room drinking her scotch. Anna, of course had been watching her get ready on the whole time on her laptop in the master bedroom. She too was putting on a neglig?e and a matching silk robe for the evening. The black stiletto heels finished the look. Her phone buzzed. A text from Andrew downstairs. "The gentleman is here," it read. "Escort him up," she replied and tied up her robe. From time to time she had employed the services of a few men from a certain discrete agency. It was just so much easier then dealing with the dating scene of Manhattan. Sure, she fucked men she met as well, but sometimes she just didn?t want to deal with the whole rigamarole. She hadn?t needed them for these last eight months but with Lauren?s situation, let?s face it, she needed a real man. More particularly for her plan, Lauren needed a real man. Lauren needed to feel a warm cock in her ass and hot cum slide down her throat. Anna became moist just thinking about it. Plus, this was one of the final benchmarks she had set for herself in this experiment. She?d have to start figuring out how to wind this whole thing down as well so she could get on with her own life. "Hello again. Robert isn?t it," Anna said meeting the two men at the top of the stairs. "I see Andrew has gotten you a drink. Excellent," she said motioning to the glass of brown liquid he held. She offered Robert her hand, lightly, feeling her own feminine nature take hold. He was one of her favorites. "Good memory. Hester, isn?t it?" Robert responded. A smile broke out on his rugged face. "Indeed," Anna confirmed. Hester Prynne, the good woman gone bad she thought. "Thank you, Andrew, I?ll see to Robert from here." "Let me know if you need anything," Andrew said and retreated down the stairs. "Shall we settle up and get that out of the way?" "Yes, that?s always a good start," said Robert. "It is double the usual, I?m afraid to say. This bug going around is no joke." "Of course," Anna said nodding her head in agreement. "It is a nasty one. I?ve doubled the amount and put your usual tip in there," she said pulling an envelope out of her robe pocket and handing it to him. The agency knew "Hester" well, so he didn?t need to count the contents of the envelope. He took it and put it into the inside pocket of his stylish black sport coat. "Come, let me explain what we will be doing tonight." Anna walked him down to Lauren?s door and explained what she wanted for the evening. Robert said he understood, and she knocked on Lauren?s door. "Come in," came the reply Anna opened the door and focused her eyes on Lauren?s face to see her reaction when Robert walked in. Lauren was sitting on the soft bench at the end of the bed with half a glass of her scotch still in her hand. She beamed at Anna and then literally whelped as Robert walked in. Blood ran to her face and she froze. "That?s right my pet, there is nowhere to run," Anna thought, relishing the lovely look of terror on Lauren?s face. "Lauren, I?d like to introduce you to Robert. Robert, this is my dear friend Lauren whom I told you about. She may be a touch shy as she?s never really been with someone of your, er...virility. Lauren, I?ve asked Robert here to entertain us tonight, won?t that be fun," she said again studying Lauren?s worried face. Lauren finished her drink in one gulp hoping the amber liquid would calm her rising fear. "Oh, I see you?ve finished your drink, darling. Let me send up another," Anna said devilishly. She pulled her phone from her other pocket of her robe and called down to Andrew. "Be a dear, will you and bring up a bottle of Dalmore, a bucket of ice and one more glass. I think we?ll need some liquid encouragement." The Dalmore was a crazy expensive bottle but if this wasn?t an occasion for her to partake, nothing was. Besides, it was going to be an amazing show. "Not to worry, Lauren, dear, help is on the way. Now, Robert, why don?t you use the closet to undress," she said motioning to the walk- in closet. "Sure thing, Hester. And nice to meet you Lauren. You look amazing this evening, if you don?t mind me saying so," he said, smiling. Lauren turned another shade of red. "Ah...thank you," Lauren got out, weakly. Robert turned and entered the closet, closing the door softly behind him. Lauren waited for the door to close and sprung to her feet. "What the fuck, Anna!" Lauren whisper shouted at her lover. "Who is this and why did he call you "Hester"?" "You haven?t read your Hawthorne! She?s the main character in the Scarlet Letter. Robert is from an agency I use from time to time. We don?t really use our real names, plus it?s just a little more intrigue. Let?s you be who you want to be. Anyway, he is here as my gift to you so you can finally experience what you?ve been wanting to," she said coming close to Lauren. She studied Lauren?s red face. "I know how you loved our time together with the dildo. This is going to be much better," she said. Anna reached up and tenderly moved a strand of hair back over Lauren ear. "He?s right, you do look as lovely as I?ve ever seen you." She moved close and kissed Lauren tentatively. Sensing her respond, Anna put her hands lightly around her and kissed more fully. Their tongues met and Lauren seemed to relax some. Soon she embraced Anna and was kissing Anna back fully when Robert came back in only black satin boxers. "Well I guess we?re ready to get started!" he said enthusiastically. "Oh, I think we?re more then ready Robert," Anna said in a sultry voice, breaking away from Lauren. A knock came at the door. "Oh, perfect timing. Come in Andrew," Anna called out. Andrew came in with a tray and carried it to the dresser opposite the bed. Anna took a few steps over to Robert telling him he was to start with Lauren. Lauren watched as Andrew put the tray down and returned to the door. He spun around catching Lauren?s eye and motioning his thumb to Robert. He mouthed "He?s gorgeous!!" then gave her a wink and closed the door. Lauren smiled. She took a breath and walked to the dresser for another drink, her reflection coming into the mirror as she approached. She studied herself, checking that her lipstick was still in place. The outfit did suit her she decided again. She had enjoyed the time with Anna the week prior and had been using the dildo after Anna gave it to her. It was her only sexual outlet at this stage. Besides, her fantasies weren?t about dildos, they were about real men. Real men who really penetrated her. Looking to the mirror again, she resolved to take this step and try to enjoy the night. "Hester, can I make you a drink?" She smiled, amused at the alias. She had read the Scarlett Letter years ago in high school and she remembered the character. Actually, deep down she knew Anna was nothing like the character in Hawthorne?s novel. She was way beyond what Hester was. "Yes, thank you dear. Two fingers, neat." "Robert?" she asked over her shoulder. "Sure, why not," he downed the remainder of his first drink and brought the glass to Lauren. Lauren started with his drink. "More ice," she asked, trying to be demure. "Please." Lauren plopped two more cubes into each of the two glasses, his and hers, and un-stoppered the bottle. She poured a good measure of the liquor into his glass and turned, handing it to him before pouring out her drink. "Thank you very much," he said and walked back to the middle of the room first smelling the aroma then taking a sip. "That is a fine scotch. Wow" "Thank you, Robert. Yes, it is a nice scotch. Celebratory." Lauren poured two fingers into the remaining empty glass Andrew had brought, stoppered the bottle and picked up both drinks. She casually walked back to Anna. "For me," Lauren said, taking control of the moment. She handed the drink to Anna. Then draped her arm around Anna?s back, thinking of seducing Robert. "We?ve been cooped up so long, I asked Hester if we could do something special tonight," she lied. "I had no idea she would bring such a, ah...specimen to me. Thank you dear," she said, kissing Anna again passionately. Anna, secretly amazed and delighted by Lauren?s seeming acceptance of the situation, genuinely kissed her back as she was becoming aroused herself. Lauren broke off the kiss and turn her attention to Robert who was clearly enjoying watching them kiss. She casually struck a pose, taking a sip from her glass without taking her eyes off him. As the smooth brown liquid descended her throat, she moved toward Robert. She came up close to Robert who was a couple inches taller and square in the shoulder. She reached up and put her hand on his bare, chiseled chest. His warm skin wasn?t at all soft but hard and firm from years of working out. He was tanned and muscled, trim but big. She guessed he probably made a lot of money in his line of work. She could never have as Lorne. "So, what do you think Robert? Can you give me something special tonight?" "Yes ma?am, I believe I can," he said gently leaning in to kiss her. She reached her free hand around his head and he used his free hand to pull her in by the waist, and they kissed for some time until Lauren could feel his member start to rise in his shorts. There was something electric about kissing him, like it was forbidden. It just made it all that much more exciting to her. She pulled back and took a step away to calm her rising nerves. There was a man with an erection in front of her. She took deep breath and then a sip of the drink before looking around to find Anna. Anna had retreated to one of the lush chairs on the other side of the room, an optimal vantage point to view the coming action. "Do continue," she called out. "I want to watch this round before I take my turn." Lauren again bolstered by her determination, turned to Robert and took his hand. She led him to the side of the bed, took his drink and placed both the drinks on the bedside stand. She faced him again and put both hands around his head and kissed him again, using her tongue liberally. She had decided again, right there, that she was all in. Robert was now fully erect, she could feel. She broke away from the kiss and opened the nightstand drawer pulling out the KY jelly next to the dildo. She held it up to him and he took it from her. "I assume you know what to do with that?" she asked. "I believe I do," he said pulling two condom packages out of the waistband of his boxers. Lauren grabbed his satin boxers and pulled them down to his ankles. As she looked up, she came face to face with his massive member, erect and proud. She steeled herself as her nervousness tried to work its way back into thoughts. She placed her colored fingertips onto his man flesh and stood up, gently stroking another man?s cock for the first time in her life. Another thrill ran through her chasing away the revulsion. She turned around, back to him, and reached down unsnapping her body suit from between her legs while he prepared himself. He was ready and waiting when she bent from the waist putting her hands on the bed. As she waited for Robert to enter her, she stole a glance at Anna. She sat there, legs crossed, elbow resting on the armchair, glass of scotch in her hand near her face in rapt attention to the unfolding action. She felt his fingers spread her cheeks and lubricate her opening, cool and wet. Soon, she felt the condomed covered tip of his shaft, also well lubricated push into her slowly. She tried to relax then thought of something. "Don?t finish in me. I want to take you in my mouth and finish you," she said, as he pushed all the way in. She let out a low grown as his cock filled her unpleasantly. He pulled out, then back in lubricating her more fully and she concentrated on relaxing. Soon he was working back and forth at an accelerated rhythm and the familiar, more pleasant feeling returned. She focused on the notion that she was being fucked by a real, flesh and blood man. Thoughts came running into her mind, thoughts that she could never have known Anna had put there over weeks and weeks of "therapy? sessions. She was his to fuck. She was his conquest. She was his little bitch. She liked men?s cocks She wanted it... She let out another groan as her own weak dick came alive ready to attempt to let out whatever release it could. She opened her eyes again and tried to focus, looking at Anna again. Her legs were uncrossed, and her robe was open to the waist, one hand still holding the scotch, the other buried deep into the front of her panties, stroking her own sex. She closed her eyes again and soon was panting, almost grunting with each of his thrusts. Faster and faster he went for several minutes, slapping her soft ass with his thighs. She let out a long groan and again, came into her own hand, shifting to a satisfying moan as she did. Anna, for her own part, was in a different kind of ecstasy. Yes, she was aroused and masturbating while she watched, but more than that, she was watching the outcome of years of planning and work. It was simply delicious watching that poor sap Lorne take it up the ass like the little bitch he was. She had turn him. She had turned him and made her woman with real heterosexual needs. A woman who wanted men just as Anna had planned it. Without changing her facial expression, Anna closed her eyes and came all over her finger. Robert, seeing that she had released...whatever that was into her own hand, slowed his pumping and slowly pulled out, careful to hold the end of the condom so it pulled out with him. "Oh, my god, it feels good to cum," she said into the bedspread. "I?ll just clean up and come back in a jiff," Robert said. "Take your time," Lauren said calling after him and reaching for a tissue to clean off her own hand. She pulled up on the bed and saw the Anna was still working her hand back and forth in her panties, eyes closed as if deep in thought. Lauren rose up from the bed and walked purposefully over to Anna, climbing on to her, knees on either side of her hips and began kissing her passionately. "Did you enjoy that?" "I did, very much," said Anna, a grin returning to her face. "More than you will ever know," she thought to herself "Do you want to watch me swallow him down, like a good girl," she said, not knowing where those words had come from. "Yes, Lauren. I want you to be a good girl and swallow every last drop of him," she said lasciviously. "It?s what you want, isn?t it darling?" she asked, almost cumming again with the thought of the power she had over this poor creature. It was exactly what she wanted, and Lauren was suddenly excited. Robert walked in and Lauren beckoned him over to the chair. She stood up and repositioned herself and Anna so that she could sit between Anna?s legs, back to her, only half her rear on the chair. "Hester wants to watch me swallow you. Would that be ok, Robert?" she asked in her own prurient tone. "She?s paying the bill, the lady should get what she wants," said Robert amiably. "I agree," said Anna. "Come closer then," she command, given him a lustful look. He did as he was told and Lauren came face to face, again, with his massive cock. The one she had just taken up the rear. She again took a breath to steel her resolve and fight her rising nerves. She focused on what she wanted, and imagined his hot cum in her mouth, an image planted there by weeks of Anna?s conditioning. She reached out with her left hand and began stroking his cock, looking up into his face. He had strong blue eyes. It occurred to her that she was attracted to men now, though she couldn?t understand when that had happened. Her thoughts were scattered when Anna reached around and put her hand on Lauren?s small breast, stroking it through the lovely pink silk satin. Her nipple responded quickly, giving her a little quiver. She leaned forward and took Robert into her mouth. His member was warm and soft, and she was careful not to hurt him with her teeth. She was tentative at first, but soon took him as far into her mouth as she could, lubricating him. She worked the head of his penis while her hand pumped the shaft. Somewhere in the back of her mind she probably knew this should be wrong but all she could think of was how much she liked this feeling. She began to wonder what his orgasm would taste like. Anna continued her victory dance behind her, thrilled at watching her little Lorne taking another man?s cock into his mouth. "That?s it dear, suck him dry like I commanded you to," she thought, evilly, letting her pride shine for the moment. She slipped her hand off her breast and down to Lauren?s little soft penis, gently stroking it. Anna?s other hand had resumed its workout of her own sex and Lauren could feel it moving around against the back of her ass. And there it was, everyone was being wacked off at once. For several minutes they all kept it up, pumping and sucking and rubbing. Anna leaned forward and whispered into Lauren?s ear, "Beg for him to cum." Lauren didn?t hesitate but looked up into his blue eyes "Please, baby," she said taking her mouth from his cock. "Cum for me," she begged. Lauren redoubled her efforts and within moments, was rewarded with a grunt and hot ropes of cum shot from his manhood. She had felt is cock flex and twitch and knew it was coming but she still almost let some of it spill from her mouth. She pumped even faster with her left hand, her arm growing weary from the effort, and swallowed all he could give her down as fast as he could spurt it into her mouth. Anna, Lauren could tell from her breathing, had also cum on her fingers. Soft moans came to her ears from behind her. Lauren pumped a little while longer, catching every last drop. She made a point to let the last drop of cum hang of his cock before she licked it from him, savoring the last of the salty taste in her mouth. She took him into her mouth again and gave him one last long suck, licking clean his wonderful cock. She liked that beautiful cock. Liked sucking him dry and particularly liked that wonderful salty cum he gave her. Lauren stood up and went around to fetch the drinks. She returned and gave him his drink, clinking hers to his as she did and taking a liberal sip to cleanse her mouth. "That was fantastic, baby," she said reaching up and kissing him. "I?ll say. What?s next? Hester, are you ready?" The party moved to the bed and soon, Anna had him between her legs enjoying his wonderful girth in her loins. Lauren lay beside her kissing her and suckling her wonderful nipples as she orgasmed over and over. She moaned and gasped in ways that Lorne had never made her, and it dawned on Lauren that perhaps she had never really satisfied Anna in her former body. After almost an hour, both Anna and Robert were spent. Robert again washed himself up in the bathroom before donning his clothes. He bid the two women, now lounging on the bed in each other?s arms, good night and left the room, closing the door behind him. Chapter 10 The summer months passed, a blur of quarantined monotony. The two worked during the weekdays and lounged by the pool on the weekends. Anna had so ingrained the persona of Lauren by the end of the summer, she doubted, clinically, that Lorne could ever come back. Her experiment was utterly and completely a success. She looked at Lauren sitting next to her on the lounger, the straps of her bikini top undone so she could even her tan onto her glistening oiled chest, a small bulge in the front of her bikini bottoms. It was now the end of August and Anna was preparing to start splitting her time in the city at the office and out in the Hamptons. Lauren had proven to be a most effective assistant and an even better art collector, but she was damned if she?d bring a tranny into the offices. The final step needed to be taken but for her own competitive nature, Anna needed Lauren to choose to undergo surgery. It wasn?t a fair fight, of course, she had manipulated the poor girl so adeptly but even still, she wanted to hear Lauren ask her for it. The experiment couldn?t end in her mind until Lorne was completely gone, making the final sacrifice to his new female persona. "Lauren, honey," she said casually, flipping the pages of her Vogue magazine behind her large sunglasses. "Hmm," Lauren responded lazily. "Don?t you think it?s time you did something about that little bulge in your shorts, dear?" Lauren opened her eyes and glanced down at her small mound in her bikini then turned her head toward Anna. "What do you mean," she asked Anna continued flipping the pages taking in the wonderful models in their high fashion poses. "I mean aren?t you ready to be who you always wanted to be, darling? Aren?t you ready to get rid of that... "thing" between your legs?" she said gesturing toward Lauren?s lower half without taking her eyes from the pages in front of her. Anna waited for the response. "Oh...I don?t know. I hadn?t really thought about it I guess." "Huh," came Anna?s reply. "I would have thought that was all you would be thinking about. You?re such a gorgeous girl. I would have thought you were just ready to be a girl finally." She let the words sit there, knowing the affect they would have on her tender psyche. "I...I guess...I thought I was a girl," Lauren said now thinking hard about Anna?s words. "Well," said Anna casually, "you are girly, that?s for sure." She lowered the magazine down to her chest and looked over to Lauren. "Aren?t you ready to be a woman, though? A real woman?" she asked, again pausing. "I mean...yes. I guess so." "Hmm. Don?t get me wrong, dear, the hormones you decided to start taking have done a wonderful job. You look so beautiful these days. I just thought you were more determined than that is all." The devilish words worked their way into her brain, planting the seed. Lauren?s mind started to swirl, and she sat there silently mulling things over. Anna returned to her magazine leaving Lauren alone to her thoughts. When she was done with the Vogue, Anna got up and retreated to the house for a nap. It wasn?t until late morning the next day when Lauren came into Anna?s office that she had courage to bring it up again. "You?re right Anna. I?ve been living a lie," said Lauren coming and sitting at the chair by the side of Anna?s desk. "I?ve spent the night anguishing over the question you asked me and you?re right. I?m not a woman, but I want to be. You?ve done so much for me already and I know I shouldn?t ask. It isn?t fair to ask...but, well..." she stammered, trying to find the courage. "I guess what I mean is...would you help me, you know...get the surgery," she said the last words barely making it from her lips. Anna smiled at hearing the magic words. She had won. She had finally and truly won. "Will I pay for your surgery, you mean?" Anna asked making a point to look into Lauren?s eyes. She didn?t want to make it too easy. Lauren couldn?t keep eye contact, the redness started flushing across her checks as she felt ashamed for asking. "Yeah, I guess," Lauren said softly studying her shoes. "I could work it off," she said hopefully. "With interest," she added, knowing she was talking to a financial powerhouse. There wasn?t much conviction in her words though, knowing it would take her years to do that. There was a long pause as Anna left her on the hook, dangling like so many caught fish foolish enough to take the bait. "Don?t be silly dear. Of course I will help you. I am nothing if not charitable. Plus, as your psychiatrist, I?m in a position to make this easy for you. There will be no delay or additional psychological appraisals. I made a few calls already this morning. The hospitals are so desperate for elective surgery to come back they?ll take you next week," she said. Anna reached over and put her hand on top of Lauren?s hand. "I?m proud of you dear. You?ve made a wonderful decision. And don?t you worry about a thing, I?ll take care of everything." Game, set, match. EPILOGUE [Two Year?s Later] Lauren unlocked the door to her Manhattan gallery, careful not to spill her Starbuck?s coffee as she first pulled open the large door and then locked it behind her. The opening was only a day away and she had to meet Anna early to finalize the details before Anna headed into the office. She quickly walked to her desk upstairs, the high heels of her shoes making a satisfying click on the hardwood floors. Anna had been insistent that Lauren be dressed immaculately at all times while she was in the gallery and she was careful to smooth the skirt of her designer dress as she sat down. After all, she represented not only the high-end world of art, but also Anna herself, the main investor in the gallery. If she was honest, she?d grown fond of high heeled shoes and the designer clothes and looked forward to getting dressed every day. She spent a few minutes reacquainting herself with the numbers and plans before she heard Anna downstairs. "Lauren darling, I?m here," she called out amiably. She also had keys to the front door. "In the office Anna," she called out and stood up, coming around the desk to wait for her benefactor. She took a moment to look at her appearance again in the mirror. The dress, sophisticated and understated, fit her shapelier figure well. Her breasts, now a C cup, filled out the front nicely and her hips and ass were rounded as they should be. She fluffed her hair out a bit with her hands and checked her makeup. She ran one hand down her throat, pleased at how flat the chondrolaryngoplasty had made her neck. The facial feminization surgery had softened her features as well; her nose, check bones and chin had all been reduced and her brow line transformed. It had taken her a while to get over not having Lorne?s penis anymore, but in all, she looked and felt like a real woman now. And Bennet certainly made good use of her new vagina. "Hello, darling." Anna said giving Lauren a hug and a kiss on each cheek, her expensive handbag hanging from the crook in her elbow. "I love that dress on you!" Lauren appreciated the complement. She was always thrilled to hear praise from Anna, and she was always terrified she would let her down somehow. Thankfully, to date she never had and the year and a half she worked for Anna at the firm after the surgery had been fruitful for both of them. Lauren had been seeding the idea of a gallery ever since they had met and finally Anna had relented. She knew Lauren had a good eye for art and artistic talent and frankly she needed new and interesting things to do with her money. Besides, there was lots of interesting financial things one could do within the context of an art gallery. Things the government might frown upon, but which are hard to prove to a grand jury. Lauren was only too happy to do whatever Anna asked her to do, which was usually something to do with using the art as an instrument in some sort of shady deal. Lauren didn?t really follow the exact parts of these transactions, Anna always handled the paperwork, but she didn?t really care either. Just so long as she had her gallery and the art business. She knew enough to make sure everything looked legitimate and left the rest to Anna. "Are we all set for tonight? I saw the Picasso is hung." "Yes, Anna, I think we?re all set. I?m very excited. The catering and booze are all lined up. The staff is ready and everyone on your list has RSVP?d. Oh, and I?ve confirmed the press will be here. The photographer from Vogue is coming as well to take shots of their creative director when he gets here." "Excellent! Well done. I guess we?re all set. Now, I have another matter to discuss with you. I?ll need you in St. Petersburg with me in two weeks. There is a gentleman there whom we would like to invest in our next fund. He also has a rather extensive art collection" she said stepping close to Lauren, her delicate perfume filling her nostrils as she did. "I think you?ll enjoy looking through his collection and discussing it with him. It is very important to him," she paused and looked into Lauren?s sweet face. "And... I think he?ll enjoy meeting you as well," she said reaching up and stroking Lauren?s soft hair. "Maybe don?t tell that boy scout of yours, Bennet, what you?re doing there, hmm? We wouldn?t want him to find out about anything that would spoil your wedding plans," she said softly, still gently stroking her hair. "Of course not, Anna," she said leaning her head into Anna?s hand, soaking in the attention. "He doesn?t need to know what we do on our trips." "That?s my girl," Anna said, now gently cupping Lauren?s cheek with her hand. "That?s why I keep you around." She paused to let the word sit with her before she again spoke. "Now, I must get to the office. Walk me out and I?ll leave you to it." The ladies walked to the front door and hugged again. Lauren opened the door stepping out to the street to hold it open. Anna walked straight to her car and got in. As she turned to go back in, Lauren looked up the block and saw a familiar face. Bennet was walking straight toward her, coffees in hand. Lauren smiled and waited for him. "Hello darlin?" Bennet said, giving his finance a kiss on the check. "I brought you coffee!" he said cheerfully. "Oh, thank you, honey, that?s so sweet of you. But I?ve already got one upstairs," she said pouting. "Not to worry. I can drink both," he said amiably, walking into the gallery as she held the door for him. "Was that Anna I saw leave?" "Yes indeed. She was checking up on the status for tomorrow night?s opening," Lauren said, spinning the large engagement ring on her left ring finger. It had only been a few weeks since he?d proposed, and she hadn?t gotten used to it being there just yet. She still had a little thrill every time she caught sight of it on her manicured finger. "I have to say, I can?t believe you are still working with her after everything she did to you. I mean, don?t get me wrong, I love who you are now, but still. That?s a lot to forgive." Lauren pulled Bennet to her and kissed her betrothed on the lips. Despite Anna?s reproach, she loved that he was such a boy scout. "You?re looking at it all wrong? It was all part of my plan," she said gesturing around to the gallery they stood in. "We have this, the Central Park Tower apartment, the cars, the art, her jets to use. She?s made me a millionaire many times over. We?ve got it all, baby." He gave her a playfully questioning look. "I don?t know honey..." he said in mild disbelief. "Ok, I didn?t know exactly what she was doing while I was hypnotized, at least not until the time I woke up when she thought I was still under. I certainly didn?t know what the shots were doing to me until it was too late. But I got my gallery in the end just like I planned. And, best of all, I got you." "Uh huh," he said still questioning her. "Look, yes, she?s a sociopath, or whatever. But she?s my sociopath and she gives me everything I want," she said with a devilish look. "?Keep your friends close?...?" "And your enemy?s closer?" "Exactly." Please read more of my stories at https://www.deviantart.com/aliceduffield and https://www.patreon.com/user?u=24221022&fan_landing=true And I would love your feedback, even just a short sentence or two! Thanks!! Alice